VANGUARD NEW YORK INSURED TAX FREE FUND
485BPOS, 1996-03-22
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<PAGE> 



=============================================================================

 
                      SECURITIES AND EXCHANGE COMMISSION 
 
                            Washington, D.C. 20549 


 
                                  FORM N-1A 


    
                  REGISTRATION STATEMENT (NO. 33-2908) UNDER
                          THE SECURITIES ACT OF 1933 
                        PRE-EFFECTIVE AMENDMENT NO.   
                       POST-EFFECTIVE AMENDMENT NO. 11 
                                     AND 
 
             REGISTRATION STATEMENT UNDER THE INVESTMENT COMPANY 
                                 ACT OF 1940 
                               AMENDMENT NO. 13 
    


 
                          VANGUARD NEW YORK INSURED 
                                TAX-FREE FUND 
              (EXACT NAME OF REGISTRANT AS SPECIFIED IN CHARTER) 


 
                                P.O. BOX 2600, 
                            VALLEY FORGE, PA 19482 
                   (ADDRESS OF PRINCIPAL EXECUTIVE OFFICE) 


 
                 REGISTRANT'S TELEPHONE NUMBER (610) 669-1000 
 
 
                        RAYMOND J. KLAPINSKY, ESQUIRE 
                                 P.O. BOX 876 
                            VALLEY FORGE, PA 19482 

    
   
   It is hereby requested that this filing become effective on March 29, 1996, 
pursuant to paragraph (b) of Rule 485. 
    
    
   Approximate Date of Proposed Public Offering: As soon as practicable after 
this Registration Statement becomes effective*. 
    
   
   Registrant elects to register an indefinite number of shares pursuant to 
Regulation 24f-2 under the Investment Company Act of 1940. Registrant filed 
its Rule 24f-2 Notice for the year ended November 30, 1995 on January 25, 
1996. 
    


==============================================================================

<PAGE>



                   VANGUARD NEW YORK INSURED TAX-FREE FUND 
 
                            CROSS REFERENCE SHEET 

<TABLE>
<CAPTION>


 Form N-1A 
Item Number                                                      Location in Prospectus 
<S>                <C>                                           <C>                      
Item 1.           Cover Page .................................   Cover Page 
Item 2.           Synopsis ...................................   Not Applicable 
Item 3.           Condensed Financial Information ............   Financial Highlights 
Item 4.           General Description of Registrant ..........    Investment Objective; Investment           
                                                                 Limitations; Investment Policies; 
                                                                 General Information 
Item 5.           Management of the Fund .....................   Investment Adviser  
                                                                 Management of the Fund; 
Item 6.           Capital Stock and Other Securities .........   Opening an Account and Purchasing    
                                                                 Shares; Selling Your Shares; The     
                                                                 Share Price of the Fund; Dividends,  
                                                                 Capital Gains and Taxes; General     
                                                                 Information 
Item 7.           Purchase of Securities Being Offered .......   Cover Page; Opening an Account and 
                                                                 Purchasing Shares 
Item 8.           Redemption or Repurchase ...................   Selling Your Shares 
Item 9.           Pending Legal Proceedings ..................   Not Applicable 
        
 Form N-1A                                                       Location in Statement 
Item Number                                                      of Additional Information 
Item 10.          Cover Page .................................   Cover Page 
Item 11.          Table of Contents ..........................   Cover Page 
Item 12.          General Information and History ............   Management of the Fund 
Item 13.          Investment Objective and Policies ..........   Investment Limitations; Investment 
                                                                 Policies 
Item 14.          Management of the Fund .....................   Management of the Fund;            
                                                                 Investment Management   
Item 15.          Control Persons and Principal Holders of                 
                  Securities .................................   Management of the Fund  
Item 16.          Investment Advisory and Other Services .....   Management of the Fund;           
                                                                 Investment Management   
Item 17.          Brokerage  Allocation ......................   Not Applicable 
Item 18.          Capital Stock and Other Securities .........   Financial Statements 
Item 19.          Purchase, Redemption and Pricing of            
                  Securities Being Offered ...................   Purchase of Shares; Redemption of    
                                                                 Shares                               
Item 20.          Tax Status .................................   Appendix 
Item 21.          Underwriters ...............................   Not Applicable 
Item 22.          Calculations of Yield Quotations of 
                  Money Market Fund ..........................   Calculation of Yield 
Item 23.          Financial  Statements ......................   Financial Statements

 
</TABLE>
<PAGE>

===============================================================================
VANGUARD
  NEW YORK
  INSURED
TAX-FREE FUND                                    A Member of The Vanguard Group
=============================================================================== 
PROSPECTUS-March 29, 1996 
- ----------------------------------------------------------------------------- 
NEW ACCOUNT INFORMATION: Investor Information Department-1-800-662-7447 (SHIP) 
- ----------------------------------------------------------------------------- 
SHAREHOLDER ACCOUNT SERVICES: Client Services Department-1-800-662-2739 (CREW) 
- --------------------------------------------------------------------------------
INVESTMENT          
OBJECTIVE & 
POLICIES            Vanguard New York Insured Tax-Free Fund (the "Fund") is an  
                    open-end non-diversified investment company that seeks to  
                    provide income that is exempt from federal and New York     
                    personal income taxes. The Fund will invest primarily in    
                    securities issued by New York state and local governments   
                    and public financing authorities, but may also invest in    
                    securities of issuers other than New York and its political 
                    subdivisions. The Fund is available only to New York        
                    residents. Shares of the Fund are neither insured nor       
                    guaranteed by any agency of the U.S. Government, including  
                    the FDIC.                                                   
- --------------------------------------------------------------------------------
OPENING AN 
ACCOUNT             Please complete and return the Account Registration Form. If
                    you need assistance in completing this Form, please call the
                    Investor Information Department, Monday through Friday, from
                    8:00 a.m. to 9:00 p.m. and Saturday, from 9:00 a.m. to 4:00
                    p.m. (Eastern time). The minimum initial investment is
                    $3,000 or $1,000 for Uniform Gifts/Transfers to Minors Act
                    accounts. The Fund is offered on a no-load basis (i.e.,
                    there are no sales commissions or 12b-1 fees). However, the
                    Fund incurs expenses for investment advisory, management,
                    administrative and distribution services.
- --------------------------------------------------------------------------------

ABOUT THIS          
PROSPECTUS          This Prospectus is designed to set forth concisely the     
                    information that you should know about the Fund before you 
                    invest. It should be retained for future reference. A      
                    "Statement of Additional Information" containing additional
                    information about the Fund has been filed with the         
                    Securities and Exchange Commission. This Statement is dated
                    March 29, 1996, and has been incorporated by reference into
                    this Prospectus. It may be obtained, without charge, by    
                    writing to the Fund or by calling the Investor Information 
                    Department.                                                
- --------------------------------------------------------------------------------
TABLE OF CONTENTS 
<TABLE>
<CAPTION>

                                               Page                                                   Page
<S>                                             <C>    <C>                                             <C>
Fund Expenses ..............................      2    Investment Adviser .........................     14 
Financial Highlights .......................      2    Dividends, Capital Gains and Taxes .........     15 
Yield and Total Return .....................      3    The Share Price of the Fund ................     16 
            FUND INFORMATION                           General Information ........................     17 
Investment Objective .......................      4                  SHAREHOLDER GUIDE                     
Investment Policies ........................      4    Opening an Account and                              
Investment Risks ...........................      5      Purchasing Shares  ........................    18 
Who Should Invest ..........................      7    When Your Account Will Be Credited .........     21 
How to Compare Tax-Free and                            Selling Your Shares ........................     21 
 Taxable Yields ............................      8    Exchanging Your Shares .....................     24 
Implementation of Policies .................      9    Important Information About Telephone               
Investment Limitations .....................     13      Transactions  .............................    26 
Management of the Fund .....................     14    Transferring Registration ..................     26 
                                                       Other Vanguard Services ....................     27 

</TABLE>
- --------------------------------------------------------------------------------

THESE SECURITIES HAVE NOT BEEN APPROVED OR DISAPPROVED BY THE SECURITIES AND
EXCHANGE COMMISSION OR ANY STATE SECURITIES COMMISSION, NOR HAS THE SECURITIES
AND EXCHANGE COMMISSION OR ANY STATE COMMISSION PASSED UPON THE ACCURACY OR
ADEQUACY OF THIS PROSPECTUS. ANY REPRESENTATION TO THE CONTRARY IS A CRIMINAL
OFFENSE.
- --------------------------------------------------------------------------------


<PAGE>

   
FUND EXPENSES       The following table illustrates all expenses and fees that
                    you would incur as a shareholder of the Fund. The expenses
                    and fees set forth in the table are for the 1995 fiscal
                    year.



                    Shareholder Transaction Expenses
                    ------------------------------------------------------------
                    Sales Load Imposed on Purchases  ...............     None  
                    Sales Load Imposed on Reinvested Dividends  ....     None  
                    Redemption Fees*  ..............................     None  
                    Exchange Fees  .................................     None  
                    Annual Fund Operating Expenses 
                    ------------------------------------------------------------
                    Management & Administrative Expenses  ..........     0.17 % 
                    Investment Advisory Expenses  ..................     0.01  
                    12b-1 Fees  ....................................     None 
                    Other Expenses 
                       Distribution Costs .....     0.02%          
                       Fund Insurance .........     0.00  
                       Miscellaneous Expenses .     0.02  
                                                  ------ 
                    Total Other Expenses ...........................      0.04% 
                                                                        ------- 
                         Total Operating Expenses ..................      0.22%
                                                                        =======
                    *Wire redemptions of less than $5,000 subject to a $5.00
                    charge.

                    The purpose of this table is to assist you in understanding
                    the various costs and expenses that you would bear directly
                    or indirectly as an investor in the Fund.

                    The following example illustrates the expenses that you
                    would incur on a $1,000 investment over various periods,
                    assuming (1) a 5% annual rate of return and (2) redemption
                    at the end of each period. As noted in the table above, the
                    Fund charges no redemption fees of any kind.

                     1 Year      3 Years     5 Years     10 Years 
                     ------      -------     -------     -------- 
                      $2           $7          $12          $28

                    This example should not be considered a representation of
                    past or future expenses or performance. Actual expenses may
                    be higher or lower than those shown.
- --------------------------------------------------------------------------------
FINANCIAL 
HIGHLIGHTS          The following financial highlights for a share outstanding
                    throughout each period insofar as they relate to each of the
                    five years in the period ended November 30, 1995, have been
                    audited by Price Waterhouse LLP, independent accountants,
                    whose report thereon was unqualified. This information
                    should be read in conjunction with the Fund's financial
                    statements and notes thereto, which, together with the
                    remaining portions of the Fund's 1995 Annual Report to
                    Shareholders, are incorporated by reference in the Statement
                    of Additional Information and this Prospectus, and which
                    appear, along with the report of Price Waterhouse LLP, in
                    the Fund's 1995 Annual Report to Shareholders. For a more
                    complete discussion of the Fund's performance, please see
                    the Fund's 1995 Annual Report to Shareholders, which may be
                    obtained without charge by writing to the Fund or by calling
                    our Investor Information Department at 1-800-662-7447.
    
   
2

<PAGE>


<TABLE>
<CAPTION>
   
                                                                           
                                                                                           
                                                  Year Ended November 30,                          
                                    -----------------------------------------------------           
                                      1995        1994        1993       1992       1991   
                                    ----------------------------------------------------- 
<S>                                   <C>        <C>         <C>        <C>                
Net Asset Value, Beginning of                                                    
   Period                             $9.70      $10.97      $10.45     $10.04     $9.66   
                                    ---------   ---------    --------   -------- --------   
Investment Operations                                                                       
   Net Investment Income ........      .581        .588        .594       .631      .639    
   Net Realized and Unrealized                                                              
     Gain (Loss) on Investments .     1.310      (1.258)       .665       .410      .380    
                                    ---------   ---------    --------   -------- --------   
     Total from Investment                                                                  
        Operations ..............     1.891       (.670)      1.259      1.041     1.019    
- -----------------------------------------------------------------------------------------                                   
Distributions                                                                               
   Dividends from Net Investment                                                            
     Income  ....................     (.581)      (.588)      (.594)     (.631)    (.639)   
   Distributions from Realized                                                              
     Capital Gains  .............        --       (.012)      (.145)        --        --    
                                    ---------   ---------    --------   -------- --------   
     Total Distributions  .......     (.581)      (.600)      (.739)     (.631)    (.639)   
- -----------------------------------------------------------------------------------------                                     
Net Asset Value, End of Period ..    $11.01       $9.70      $10.97     $10.45    $10.04    
=========================================================================================                                      
Total Return  ...................     19.90%      (6.37)%     12.42%     10.63%    10.87%   
=========================================================================================       
Ratios/Supplemental Data  .......                                                           
Net Assets, End of Period                                                                   
   (Millions) ...................      $859        $695        $807       $574      $408    
Ratio of Expenses to Average Net                                                            
   Assets .......................       .22%(1)     .22%        .19%       .23%+     .27%+  
Ratio of Net Investment Income                                                              
   to Average Net Assets ........      5.51%       5.60%       5.47%      6.11%     6.48%   
Portfolio Turnover Rate  ........        10%         20%         10%        28%       19%             
                                                                                  
                                                                                 
                                                 Year Ended November 30,           April 7,        
                                    --------------------------------------------    1986 to         
                                                                                    Nov. 30, 
                                       1990       1989       1988        1987        1986** 
                                     -------------------------------------------------------- 
Net Asset Value, Beginning of 
   Period                             $9.73       $9.26      $8.87      $10.08       $10.00 
                                     --------    --------   --------   ---------   ---------- 
Investment Operations  ..........
   Net Investment Income ........      .629        .635       .618        .628         .381 
   Net Realized and Unrealized 
     Gain (Loss) on Investments .     (.070)       .470       .390      (1.210)        .080 
                                     --------    --------   --------   ---------   ---------- 
     Total from Investment 
        Operations ..............      .559       1.105      1.008       (.582)        .461 
- ---------------------------------------------------------------------------------------------                                     
Distributions  ..................
   Dividends from Net Investment 
     Income  ....................     (.629)      (.635)     (.618)      (.628)       (.381) 
   Distributions from Realized 
     Capital Gains  .............        --          --         --          --           -- 
                                     --------    --------   --------   ---------   ---------- 
     Total Distributions  .......     (.629)      (.635)     (.618)      (.628)       (.381) 
- ---------------------------------------------------------------------------------------------      
Net Asset Value, End of Period  .     $9.66       $9.73      $9.26       $8.87       $10.08 
=============================================================================================                                     
Total Return  ...................      5.99%      12.25%     11.62%      (5.82)%       5.10% 
=============================================================================================                                     
Ratios/Supplemental Data  .......
Net Assets, End of Period 
   (Millions) ...................      $241        $167       $103         $76          $52 
Ratio of Expenses to Average Net 
   Assets .......................       .31%+       .34%+      .40%+       .35%+        .34%+ 
Ratio of Net Investment Income 
   to Average Net Assets ........      6.60%       6.64%      6.75%       6.80%        6.50%* 
Portfolio Turnover Rate  ........        17%         10%         4%         31%           8%
</TABLE>

 *  Annualized. 
**  Commencement of operations. 
+   Insurance Expenses Represent .01%, .01%, .02%, .04%, .07%, .08% and .08%, 
    respectively. 
(1) Effective in fiscal 1995, does not include expense reductions from directed 
    brokerage and custodian fee offset arrangements. The 1995 Ratio of Expenses 
    to Average Net Assets is .21% after including these reductions. 
- -------------------------------------------------------------------------------
<PAGE>

YIELD AND 
TOTAL RETURN        From time to time the Fund may advertise its yield and total
                    return. Both yield and total return figures are based on
                    historical earnings and are not intended to indicate future
                    performance. The "total return" of the Fund refers to the
                    average annual compounded rates of return over one-, five-
                    and ten-year periods or over the life of the Fund (as stated
                    in the advertisement) that would equate an initial amount
                    invested at the beginning of a stated period to the ending
                    redeemable value of the investment, assuming the
                    reinvestment of all dividend and capital gains
                    distributions.

                    In accordance with industry guidelines set forth by the U.S.
                    Securities and Exchange Commission, the "30-day yield" of
                    the Fund is calculated by dividing the net investment income
                    per share earned during a 30-day period by the net asset
                    value per share on the last day of the period. Net
                    investment income includes interest and dividend income
                    earned on the Fund's securities; it is net of all expenses
                    and all recurring and nonrecurring charges that have been
                    applied to all shareholder accounts. The yield calculation
                    assumes that the net investment income earned over 30 days
                    is compounded monthly for six months and then annualized.
                    Methods used to calculate advertised yields are standardized
                    for all bond mutual funds. However, these methods differ
                    from the accounting methods used by the Fund to maintain its
                    books and records, and so the advertised 30-day yield may
                    not fully reflect the income paid to an investor's account
                    or the yield reported in the Fund's Annual Report to
                    Shareholders.

- -------------------------------------------------------------------------------
                                                                              3
    


<PAGE>

INVESTMENT
OBJECTIVE           The objective of the Fund is to provide investors with a    
                    high level of income that is exempt from federal and New    
                    York personal income taxes. 
               
The Fund seeks to   The Fund is available only to investors who reside in New   
provide income that York. There is no assurance that the Fund will achieve its 
is exempt from      stated objective.                                           
federal and New                                                                 
York income taxes   The investment objective of the Fund is fundamental and so  
                    may not be changed without the approval of a majority of the
                    Fund's shareholders.                                        
                                                                                
- --------------------------------------------------------------------------------
INVESTMENT 
POLICIES            The Fund will invest at least 80% of its assets in insured
                    New York municipal securities, exclusive of New York AMT
The Fund invests    bonds (see below). New York municipal securities are debt  
in insured New      obligations issued by New York state and local governments 
York municipal      and public financing authorities (and, possibly, by certain 
securities          U.S. territories) that seek to provide interest income that 
                    is exempt from both federal and New York personal income  
                    taxes. The New York municipal securities described above, 
                    may include securities in which the tax-exempt interest rate
                    is determined by an index, swap or some other formula.
                    Insured New York municipal securities are those for which 
                    scheduled payments of interest and principal are guaranteed 
                    by a private (non-governmental) insurance company.
                    
                    The insurance feature of the Fund does not guarantee the
                    market value of the municipal bonds or the value of the
                    Fund's shares. The insurance refers to the face or par value
                    of the securities in the Fund. See "Implementation of
                    Policies" for a description of the Fund's insurance feature.

                    The Fund is expected to maintain an average weighted
                    maturity between 15 and 25 years. Bonds with longer
                    maturities usually offer higher yields, but are also subject
                    to greater market fluctuations as interest rates change. See
                    "Investment Risks."

                    Normally, the Fund seeks to invest substantially all of its
                    assets in insured New York municipal obligations. However,
                    under certain circumstances, the Fund may invest up to 20%
                    of its assets in any combination of the following
                    securities:

                    o Municipal notes and variable rate demand instruments,
                      including derivative securities, rated MIG-1 or VMIG-1, or
                      P-1 by Moody's Investors Service, Inc. ("Moody's") or 
                      SP-1+, SP-1, A-1+, or A-1 by Standard & Poor's Corporation
                      ("Standard & Poor's");

                    o Uninsured, short-term municipal securities, issued in New
                      York or in other states;

                    o Certain taxable securities, including U.S. Government
                      securities; and

                    o Certain tax-exempt municipal securities issued by other
                      states that have similar characteristics to the securities
                      typically purchased by the Fund.

                    In such cases, a portion of the Fund's income may be subject
                    to New York income taxes, federal income taxes, or both.
                    (See page 16).
4

   




         
<PAGE>
                    Subject to the same 20% limit, the Fund is also authorized
                    to invest in New York AMT bonds. The income from New York
                    AMT bonds is exempt from federal and New York income taxes,
                    but may be a tax preference item for purposes of the federal
                    alternative minimum tax, see "Implementation of Policies."

                    Under unusual circumstances, such as a national financial
                    emergency, the Fund reserves the right to invest more than
                    20% of its assets in securities other than New York
                    municipal obligations. In most instances, however, the Fund
                    will seek to avoid such holdings in an effort to provide
                    income that is fully exempt from federal and New York
                    personal income taxes.

The Fund will 
diversify its 
holdings            Although organized as a non-diversified investment company,
                    the Fund intends to diversify its holdings of New York
                    municipal securities by complying with Subchapter M of the
                    Internal Revenue Code (the "Code"). In part, Subchapter M
                    requires that, at the close of each quarter of the taxable
                    year, those issuers which represent more than 5% of the
                    Fund's assets be limited in aggregate to 50% of the Fund,
                    and that no one issue exceed 25% of the Fund's total assets.
                    As of November 30, 1995, the Fund held securities of 74
                    issuers, with the largest holding representing 11.74% of the
                    Fund's assets.

                    The Fund is responsible for voting the shares of all
                    securities it holds.

                    The Fund's policy of investing at least 80% of its assets in
                    New York municipal securities under normal circumstances is
                    fundamental and may not be changed without shareholder
                    approval. The other investment policies described above are
                    not fundamental and so may be changed by the Board of
                    Trustees without shareholder approval.

- --------------------------------------------------------------------------------
INVESTMENT 
RISKS               As a mutual fund investing in long-term municipal           
                    securities, the Fund is subject to interest rate, credit,   
                    call, income and manager risk.                              
                    
The Fund is subject 
to interest rate, 
credit, call, income 
and manager risk    Interest rate risk is the potential for bond price
                    fluctuations due to changing interest rates. In general,
                    bond prices vary inversely with interest rates. If interest
                    rates rise, bond prices generally decline; if interest rates
                    fall, bond prices generally rise. In addition, for a given
                    change in interest rates, longer-maturity bonds exhibit
                    greater price fluctuations than shorter-maturity bonds. To
                    compensate investors for this risk, longer-maturity bonds
                    generally offer higher yields than shorter-maturity bonds,
                    other factors, including credit quality, being equal.
                    Interest rate risk may be increased or decreased when a fund
                    purchases derivative New York municipal securities. Such
                    derivative securities rely on sophisticated interest rate
                    calculation mechanisms. For certain types of derivative
                    bonds, the magnitude of increases and decreases in their
                    price may be proportionately larger or smaller than, or
                    inverse to, the price changes that broad market interest
                    rate fluctuations would produce in long-term bonds.

                    Credit risk is the possibility that a bond issuer will fail
                    to make timely payments of interest or principal to a fund.
                    The credit risk of a fund depends on the credit quality of
                    its underlying securities. In general, the lower the credit
                    quality of a fund's municipal securities, the higher a
                    fund's yield, all other factors such as maturity being
                    equal.
                                                                               5
<PAGE>

   
                    Call risk is the possibility that, during periods of falling
                    interest rates, a municipal security with a high stated
                    interest rate will be prepaid (or "called") prior to its
                    expected maturity date. As a result, a fund will be required
                    to invest the unanticipated proceeds at lower interest
                    rates, and the fund's income may decline. Call provisions
                    are most common for intermediate- and long-term municipal
                    bonds.

                    Income risk is the potential for a decline in a fund's
                    income due to falling market interest rates. Because a
                    fund's income is based on interest rates, which can
                    fluctuate substantially over short periods, income risk is
                    expected to vary from fund to fund.
The Fund is 
subject to 
manager risk        Finally, the investment adviser manages the Fund according
                    to the traditional methods of "active" investment
                    management, which involve the buying and selling of
                    securities based upon economic, financial and market
                    analysis and investment judgment. Manager risk refers to the
                    possibility that a fund's investment adviser may fail to
                    execute the Fund's investment strategy effectively. As a
                    result, a fund may fail to achieve its stated objective.

                    Because the Fund invests in long-term municipal bonds,
                    interest rate risk for the Fund may be high. The average
                    weighted maturity of the Fund is expected to exceed 15
                    years, meaning that the Fund's share price will fluctuate,
                    sometimes substantially, when interest rates change. The
                    following chart illustrates the potential interest rate risk
                    of the Fund. The chart shows the market value of a $1,000
                    investment in a single bond with the same yield and maturity
                    characteristics as the Fund on December 31, 1995, assuming a
                    1% and 2% point increase or decrease in interest rates:
    



   
                   Hypothetical Value of $1,000 Investment 
                   --------------------------------------- 
                                  After Change in Interest Rates of: 
                            -------------------------------------------------- 
30-Day      Average          1% Point      1% Point     2% Point    2% Point 
Yield       Maturity         Increase      Decrease     Increase     Decrease 
- ----       -----------     -----------    ----------   ----------   ---------- 
4.84%        10.5 years      $ 922         $1,086        $ 852        $1,180 
    

                    This chart is intended to provide you with general
                    guidelines for evaluating the effect of interest rate
                    changes on the Fund and determining the degree of interest
                    rate risk you may be willing to assume. The yield and price
                    changes shown are purely for illustrative purposes, and
                    should not be taken as representative of current or future
                    yields or expected changes in the share price of the Fund.
Credit risk is 
expected to be 
low                 Credit risk depends on the average quality of the Fund's
                    underlying securities and the Fund's degree of
                    diversification. The Fund invests primarily in bonds insured
                    by top-rated insurance companies against the possible
                    default of an issuer as to the timely payment of interest
                    and principal. As a result, the average credit quality of
                    the Fund is expected to be very high, and credit risk is
                    expected to be minimal.
                    Ordinarily, an investment company concentrating its
                    investments in one state, such as the Fund, would be exposed
                    to greater credit risks than an

6
<PAGE>


                    investment company investing in a nationally diversified
                    portfolio of municipal securities. These risks include
                    possible tax law changes, a deterioration in economic
                    conditions, and differing levels of supply and demand for
                    New York municipal obligations.

                    To minimize the effects of concentrating its investments in
                    New York obligations, the Fund intends to diversify its
                    holdings by complying with Subchapter M of the Internal
                    Revenue Code. (See "Investment Policies" for a description
                    of the requirements of Subchapter M.) In addition, the use
                    of municipal bond insurance should minimize the credit risk
                    associated with the Fund.
   
                    As of December 31, 1995, the top ten portfolio holdings,
                    based on market value, represented 49.6% of the Fund's net
                    assets.
    
                    The following chart summarizes credit, interest rate, income
                    and call risks for the Fund.
   
                    ------------------------------------------------------
                     Credit        Interest        Income       Prepayment/ 
                      Risk         Rate Risk        Risk         Call Risk 
                    ------------------------------------------------------
                    Very Low         High           Low           Medium
                    ------------------------------------------------------
    

- --------------------------------------------------------------------------------

WHO SHOULD 
INVEST              The Fund is intended for New York residents seeking income 
                    that is exempt from federal and New York personal income  
New York residents  taxes. As a rule, tax-free income is attractive to investors
seeking tax-exempt  in high federal and New York tax brackets. You can determine
income              whether tax-exempt or taxable income is more attractive in 
                    your own case by comparing the Fund's tax-free yield with 
                    the yield from a comparable taxable mutual fund investment.
        
                    See "How to Compare Tax-Free and Taxable Yields." 
                    Assuming that tax-free income is attractive in your own tax
                    bracket, you should weigh an investment in the Fund in terms
                    of its expected yield and price volatility, and your own 
                    investment objectives, risk preferences, and time horizon.
                    The Fund is suitable for investors who are seeking the   
                    highest, most durable streams of income and who can tolerate
                    sometimes sharp fluctuations in share price in pursuit of 
                    their income objectives. The yield of the Fund is expected 
                    to be higher, and the level of income provided more stable,
                    than that provided by other mutual funds which invest in  
                    short-term New York municipal securities. However, because 
                    of the Fund's potential price volatility, the Fund is 
                    appropriate only for those investors who can hold their 
                    investment over the long term. 
           
                    The Fund is intended to be a long-term investment vehicle 
                    and is not designed to provide investors with a means of 
                    speculating on short-term market movements. Investors who 
                    engage in an excessive amount of account activity generate 
                    additional costs that are borne by all of the Fund's 
                    shareholders. In order to minimize such costs, the Fund has 
                    adopted the following policies. The Fund reserves the right 
                    to reject any purchase request (including exchange purchases
                    from other Vanguard portfolios) that is reasonably deemed to
                    be disruptive to efficient portfolio management, either 
                    because of the timing of the investment or previous 
                     
- --------------------------------------------------------------------------------
                                                                               7
                    
    

<PAGE>

                    excessive trading by the investor. Additionally, the Fund
                    has adopted exchange privilege limitations as described in
                    the section "Exchange Privilege Limitations." Finally, the
                    Fund reserves the right to suspend the offering of its
                    shares. 
- --------------------------------------------------------------------------------
HOW TO COMPARE 
TAX-FREE AND 
TAXABLE YIELDS      Before choosing a specific tax-exempt investment, such as
                    the Fund, you should determine if you would be better off
                    with taxable or tax-exempt income for your tax bracket. To
                    compare taxable and tax-free income, you should first
                    determine your combined federal, state and local tax
                    bracket. Then you should calculate the "taxable equivalent
                    yield" for the Fund you are considering, and compare it with
                    the yield of a taxable investment with similar credit and
                    maturity characteristics.

                    1. Determine your combined tax bracket. Your combined tax
                    bracket depends on whether you itemize state and local taxes
                    as a deduction on your federal return. If you do not
                    itemize, then your combined tax bracket is the sum of your
                    federal, state and local tax brackets.

                    If you do itemize, then your combined tax bracket is
                    calculated as follows. First, calculate your effective state
                    and local tax bracket using the following formula:

                              Federal                            Effective 
                        (100% - Tax   )   X    State &     =     State & 
                              Bracket        Local Bracket     Local Bracket 
 
                    For example, if you are in a 7.6% state tax bracket, a local
                    tax bracket of 3.91%, and a 28% federal tax bracket, your
                    effective state and local tax bracket would be 8.28%:
 
                           (100% - 28%)    X       11.51%    =     8.28%

                    Second, add your effective state and local tax bracket to
                    your federal tax bracket to determine your combined tax
                    bracket:

                      Federal             Effective              Combined 
                        Tax       +        State &        =        Tax 
                      Bracket           Local Bracket            Bracket 

                        28%       +          8.28%        =      36.28%
                                  
                    2. Calculate your taxable equivalent yield. The taxable
                    equivalent yield for a fund is based upon the Fund's current
                    tax-exempt yield and your combined tax bracket. The formula
                    is:

                         Fund's Tax-Free Yield                 Your Taxable    
                    -------------------------------    =     Equivalent Yield   
                    100% - Your Combined Tax Bracket        

8
<PAGE>


                    For example, if you are in a combined tax bracket of 36.28%,
                    and the Fund's tax- free yield is 6%, the Fund's taxable
                    equivalent yield would be 9.42%:

                                   6% 
                         --------------------    =  9.42% 
                             100% - 36.28% 

                    In this example, you would choose the tax-free investment if
                    the 9.42% taxable equivalent yield were greater than the
                    taxable yield from a comparable investment (e.g., a taxable
                    bond fund of comparable maturity and credit quality).
- -------------------------------------------------------------------------------
    
IMPLEMENTATION 
OF POLICIES        The Fund's adviser uses a variety of investment vehicles to 
                   achieve the objective of the Fund.                          
The Fund invests   
in municipal       The Fund invests principally in tax-exempt New York          
bonds, notes and   municipal securities, which are debt obligations issued by   
securities derived New York state and local governments and public financing    
from  municipal    authorities (and by certain U.S. territories) that provide   
bonds and notes    interest income that is exempt from federal and New York     
                   personal income taxes. Municipal securities include both     
                   municipal bonds (those securities with maturities of five    
                   years or more) municipal notes (those with maturities of     
                   less than five years) and derivative securities (those       
                   securities in which a maturity may have been shortened by a  
                   demand feature).                      
                                                     
                   Municipal bonds are issued for a wide variety of reasons: to 
                   construct public facilities, such as airports, highways,     
                   bridges, schools, hospitals, housing, mass transportation,   
                   streets, water and sewer works; to obtain funds for          
                   operating expenses; to refund outstanding municipal          
                   obligations; and to loan funds to various public             
                   institutions and facilities. Certain industrial development 
                   bonds are also considered municipal bonds if their interest  
                   is exempt from federal income tax. Industrial development    
                   bonds are issued by, or on behalf of public authorities to   
                   obtain funds for various privately-operated manufacturing    
                   facilities, housing, sports arenas, convention centers,      
                   airports, mass transportation systems, and water, gas or     
                   sewage works.                                                
                                                                                
                   General obligation municipal bonds are secured by the        
                   issuer's pledge of full faith, credit and taxing power.      
                   Revenue or special tax bonds are payable from the revenues   
                   derived from a particular facility or, in some cases, from a 
                   special excise or other tax, but not from general tax        
                   revenue. Industrial development bonds are ordinarily         
                   dependent on the credit quality of a private authority.     
                                                                                
                   Municipal notes are issued to meet the short-term funding    
                   requirements of local, regional and state governments.       
                   Municipal notes include tax anticipation notes, bond         
                   anticipation notes, revenue anticipation notes, tax and      
                   revenue anticipation notes, construction loan notes,         
                   short-term discount notes, tax-exempt commercial paper, and  
                   demand notes. Demand notes permit an investor (such as the  
                   Fund) to demand from the issuer payment of principal plus    
                   accrued interest upon a specified number of days' notice.    
                    

The Fund may invest 
in AMT bonds        The Fund is authorized to invest up to 20% of its assets in
                    so-called "AMT" bonds. AMT bonds are tax-exempt "private
                    activity" bonds issued after August 7, 1986, whose

                                                                               9
<PAGE>
   
                    proceeds are directed at least in part to a private,
                    for-profit organization. While the income from AMT bonds is
                    exempt from regular federal income tax, it is a tax
                    preference item for purposes of the federal AMT. The
                    alternative minimum tax is a special separate tax that
                    applies to a limited number of taxpayers who have certain
                    adjustments to income or tax preference items.
    

The Fund may invest 
in Market Discount
bonds               The Fund may invest in "Market Discount" bonds when, in the
                    opinion of the Fund's adviser, the investment will be
                    advantageous to the Fund's shareholders. A Market Discount
                    bond is a bond purchased at a discount from its original
                    issue price after April 30, 1993 and with a maturity in
                    excess of one year from its issue date. In certain
                    circumstances, disposition of a Market Discount bond will
                    result in taxable ordinary income to the extent of any gain
                    realized.
   
                    Although the objective of the Fund is to provide income free
                    of federal income tax, certain market conditions may make
                    Market Discount bonds desirable investments. The Fund will
                    purchase Market Discount bonds only if the Fund's adviser
                    expects that the purchase of these investments on an
                    after-tax basis will enhance the Fund's total return.
    

Three types of 
insurance may be
used by the Fund    To provide an added level of credit protection, the Fund
                    uses three types of insurance: new issue, mutual fund and
                    secondary market insurance. A new issue insurance policy is
                    purchased by a bond issuer who wishes to increase the credit
                    rating of a security. By paying a premium and meeting the
                    insurer's underwriting standards, the bond issuer is able to
                    obtain a high credit rating for the security (usually Aaa
                    from Moody's or AAA from Standard & Poor's). New issue
                    insurance policies are non-cancellable and continue in force
                    as long as the bonds are outstanding.
   
                    A mutual fund insurance policy may be used to guarantee
                    specific bonds only while owned by a mutual fund. The Fund
                    has obtained a mutual fund insurance policy from Financial
                    Guaranty Insurance Company ("Financial Guaranty"), a
                    AAA-rated insurance company. Based upon the expected
                    composition of the Fund, the annual premiums for the policy
                    are likely to range from 0.20% to 0.40% of the principal
                    value of the bonds insured under the policy, thereby
                    reducing the Fund's current yield.
    
                    A secondary market insurance policy is purchased by an
                    investor (such as the Fund) subsequent to the bond's
                    original issuance and generally insures a particular bond
                    for the remainder of its term. The Fund may purchase bonds
                    that have already been insured under a secondary market
                    insurance policy by a prior investor, or the Fund may itself
                    purchase such a policy from Financial Guaranty for bonds
                    that are currently uninsured.
   
                    An insured municipal bond in the Fund will typically be
                    covered by only one of the three policies. For instance, if
                    a bond is already covered by a new issue insurance policy or
                    a secondary market insurance policy, then that security will
                    not be insured under the Fund's mutual fund insurance
                    policy. All of the insurance policies used by the Fund will
                    be obtained only from companies rated Aaa by Moody's or AAA
                    by Standard & Poor's at the time the insurance contract was
                    obtained.
    


10
<PAGE>


The Fund may report
an effective average
weighted maturity   The Fund observes strict maturity guidelines as set forth in
                    detail under "Investment Policies." These maturity standards
                    are specified in terms of the Fund's average weighted
                    maturity. From time to time, however, the Fund may also
                    report an effective average weighted maturity, which
                    reflects, among other items, the likelihood that a municipal
                    bond or note held by the Fund may be redeemed or "called"
                    prior to its stated maturity date. For example, if the Fund
                    consists entirely of 20-year bonds, some of which may be
                    "called" prior to their stated maturity in 20 years, the
                    Fund's average weighted maturity will be 20 years, while its
                    effective average maturity will be shorter.

                    The Fund's effective average weighted maturity will be
                    influenced by bond market conditions, and so may vary from
                    day to day, even if no change has been made to the Fund's
                    underlying investment securities. For example, if interest
                    rates decline, a greater proportion of the Fund's securities
                    may be subject to call (redemption) prior to their stated
                    maturity. As a result, reflecting this increased call risk,
                    the effective average maturity of the Fund will shorten,
                    independent of actual purchases or sales of portfolio
                    securities.
   
The Fund may
purchase when-issued
securities          The Fund may purchase tax-exempt securities on a
                    "when-issued" basis. In buying "when-issued" securities, the
                    Fund commits to buy securities at a certain price even
                    though the securities may not be delivered for a certain
                    time period. The Fund pays for the securities and begins
                    earning interest when the securities are actually delivered.
                    As a consequence, it is possible that the market price of
                    the securities at the time of delivery may be higher or
                    lower than the purchase price.
    

The Fund may lend 
its securities      The Fund may lend its investment securities on either a
                    short-term or long-term basis to qualified institutional
                    investors for the purpose of realizing additional net
                    investment income. Loans of securities by a Fund will be
                    collateralized by cash, letters of credit, or securities
                    issued or guaranteed by the U.S. Government or its agencies.
                    The collateral will equal at least 100% of the current
                    market value of the loaned securities. Income derived from
                    the lending of securities is not tax-exempt, and a portion
                    of the tax-exempt interest earned when a municipal security
                    is on loan must be characterized as taxable income.
                    Therefore, the Fund will limit such activity in accordance
                    with its investment objective.

   
The Fund may invest 
in municipal lease
obligations         The Fund may purchase municipal lease obligations, which are
                    securities issued by state and local governments to acquire
                    land, equipment and facilities. These obligations typically
                    are not backed by the issuing municipality's full authority
                    to assess taxes to meet its debt obligations. If the issuing
                    authority fails to make the appropriations necessary to
                    cover lease payments, then the lease may terminate. In
                    certain circumstances, the issuer could default on the lease
                    obligation and thereby cause a loss to investors. Also, in
                    certain circumstances, such as a default or termination of
                    the lease, all or a portion of the payments attributable to
                    the lease may be taxable as ordinary income.

Derivative
Investing           Derivatives are instruments whose values are linked to or
                    derived from an underlying security or index. The most
                    common and conventional types of derivative securities are
                    futures and options.
    

                                                                              11
<PAGE>

   
The Fund may
invest in 
derivative
securities          The Fund may invest in conventional derivative securities
                    including futures contracts and options, but only to a
                    limited extent. The Fund may enter into futures contracts
                    provided that not more than 5% of its assets are required as
                    a futures contract deposit; in addition, the Fund may enter
                    into futures contracts and options transactions only to the
                    extent that obligations under such contracts or transactions
                    represent not more than 20% of the Fund's assets.

                    Futures contracts and options may be used for several common
                    fund management strategies: to maintain cash reserves while
                    simulating full investment, to facilitate trading, to reduce
                    transaction costs, or to seek higher investment returns when
                    a specific futures contract is priced more attractively than
                    other futures contracts or the underlying security or index.
                    The Fund may not use futures contracts or options
                    transactions to leverage its assets.

                    For example, in order to remain fully invested in bonds
                    while maintaining liquidity to meet potential shareholder
                    redemptions, the Fund may invest a portion of its assets in
                    a bond futures contract. Because futures contracts only
                    require a small initial margin deposit, the Fund would then
                    be able to maintain a cash reserve to meet potential
                    redemptions, while at the same time remaining fully
                    invested. Also, because the transaction costs of futures and
                    options may be lower than the costs of investing in bonds
                    directly, it is expected that the use of futures contracts
                    and options may reduce the Fund's total transaction costs.

                    The Portfolios may use futures contracts for bona fide
                    "hedging" purposes. In executing a hedge, a manager sells,
                    for example, municipal bond futures contracts to protect
                    against a decline in the bond market. If the market drops,
                    the value of the futures position will rise, thereby
                    offsetting the decline in value of the portfolio's bond
                    holdings.

                    The Portfolios may invest in partnerships and grantor trust
                    derivative products. However, prior to the purchase of such
                    security, a determination must be made by the Fund that the
                    inherent risk of the partnership or grantor trust derivative
                    product is minimal.

Futures contracts
and options pose
risks               The primary risks associated with the use of futures
                    contracts and options are: (i) imperfect correlation between
                    the change in market value of the bonds held by the Fund and
                    the prices of futures contracts and options; and (ii)
                    possible lack of a liquid secondary market for a futures
                    contract and the resulting inability to close a futures
                    position prior to its maturity date. The risk of imperfect
                    correlation will be minimized by investing in those
                    contracts whose price fluctuations are expected to resemble
                    those of the Fund's underlying securities. The risk that the
                    Fund will be unable to close out a futures position will be
                    minimized by entering into such transactions on a national
                    exchange with an active and liquid secondary market.
                    Historically, the futures market has been more liquid than
                    the municipal bond market; therefore, the Fund's liquidity
                    may be improved by investing in futures.

                    The risk of loss in trading futures contracts in some
                    strategies can be substantial, due both to the low margin
                    deposits required and the extremely high degree of
    


12

<PAGE>

   
                    leverage involved in futures pricing. As a result, a
                    relatively small price movement in a futures contract may
                    result in immediate and substantial loss (or gain) to the
                    investor. When investing in futures contracts, the Fund will
                    segregate cash or cash equivalents in the amount of the
                    underlying obligation.


Partnerships and 
grantor trusts pose
certain risks       The primary risks associated with partnerships and grantor
                    trust derivative products are (i) the possibility of a tax
                    ruling which affects the status of the state or federal
                    opinions which are necessary to support the issuance of the
                    derivative; (ii) the possibility that the tender option on a
                    security could be withdrawn upon the occurrence of certain
                    events and (iii) the possible lack of a liquid secondary
                    market for the securities. The Fund will attempt to minimize
                    the risks of partnership and grantor trust derivative
                    products by carefully selecting which securities to purchase
                    and by constantly monitoring securities held by the Fund.
    
- --------------------------------------------------------------------------------
INVESTMENT 
LIMITATIONS          The Fund has adopted certain limitations designed to reduce
                     its exposure to specific situations. These limitations   
The Fund has         include the following:
adopted certain
fundamental         a) The Fund will invest a minimum of 80% of its net assets
limitations            in insured municipal bonds, the interest on which is
                       exempt from federal and New York personal income taxes.
   
                    b) At the close of each quarter of the taxable year, the
                       Fund will limit the aggregate value of all holdings,
                       except U.S. Government and cash items, as defined in the
                       Internal Revenue Code, each of which exceeds 5% of the
                       Fund's total assets, to an aggregate amount of 50% of
                       such assets.
    

                    c) The Fund will limit the aggregate value of holdings of a
                       single issuer (except U.S. Government and cash items as
                       defined in the Code) to a maximum of 25% of the Fund's
                       total assets. For the purposes of this limitation,
                       identification of the issuer will be based on a
                       determination of the source of assets and revenues
                       committed to meeting interest and principal payments on
                       each security.

                    d) The Fund will not borrow money except for temporary or
                       emergency purposes, and then not in excess of 10% of the
                       Fund's total assets. The Fund will repay all borrowings
                       before making additional investments, and the interest
                       paid on such borrowings will reduce income.

                    e) The Fund will not pledge, mortgage, or hypothecate more
                       than 10% of its total assets.

                       These investment limitations are considered at the time
                       investment securities are purchased. The limitations
                       described here and in the Statement of Additional
                       Information may be changed only with the approval of a
                       majority of the Fund's shareholders.
  
- --------------------------------------------------------------------------------
                                                                              13

<PAGE>
     
MANAGEMENT
OF THE FUND         The Fund is a member of The Vanguard Group of Investment    
                    Companies, a family of more than 30 investment companies    
                    with more than 90 distinct investment portfolios and total  
Vanguard            assets in excess of $190 billion. Through their             
administers         jointly-owned subsidiary, The Vanguard Group, Inc.          
and distributes     ("Vanguard"), the Fund and the other funds in the Group     
the Fund            obtain at cost virtually all of their corporate management, 
                    administrative, shareholder accounting and distribution     
                    services. Vanguard also provides investment advisory        
                    services on an at-cost basis to certain Vanguard funds. As a
                    result of Vanguard's unique corporate structure, the        
                    Vanguard Funds have costs substantially lower than those of 
                    most competing mutual funds. In 1995, the average expense   
                    ratio (annual costs including advisory fees divided by total
                    net assets) for the Vanguard funds amounted to approximately
                    .31% compared to an average of 1.11% for the mutual fund    
                    industry (data provided by Lipper Analytical Services).     

                    The Officers of the Fund manage its day-to-day operations
                    and are responsible to the Fund's Trustees. The Trustees set
                    broad policies for the Fund and choose its Officers. A list
                    of Trustees and Officers of the Fund and a statement of
                    their present positions and principal occupations during the
                    past five years can be found in the Statement of Additional
                    Information.

                    Vanguard employs a supporting staff of management and
                    administrative personnel needed to provide the requisite
                    services to the funds and also furnishes the funds with
                    necessary office space, furnishings and equipment. Each fund
                    pays its share of Vanguard's total expenses, which are
                    allocated among the funds under methods approved by the
                    Board of Trustees (Directors) of each fund. In addition,
                    each fund bears its own direct expenses, such as legal,
                    auditing and custodian fees.

                    Vanguard also provides distribution and marketing services
                    to the Vanguard funds. The funds are available on a no-load
                    basis (i.e., there are no sales commissions or 12b-1 fees).
                    However, each fund bears its share of the Group's
                    distribution costs. 
- --------------------------------------------------------------------------------
INVESTMENT 
ADVISER             The Fund receives all investment advisory services on an    
                    at-cost basis from Vanguard's Fixed Income Group. The Group 
Vanguard manages    also provides investment advisory services to more than 40  
the Fund's          Vanguard money market and bond portfolios, both taxable and 
investments         tax-exempt. Total assets under management by Vanguard's     
                    Fixed Income Group were approximately $66 billion as of     
                    December 31, 1995. The Fixed Income Group is supervised by  
                    the Officers of the Fund. Ian A. MacKinnon, Senior Vice     
                    President of Vanguard, has been in charge of the Group since
                    its inception in 1981.                                      
                                                                                
                    o David Hamlin, a Principal of Vanguard, serves as portfolio
                      manager of the New York Insured Tax-Free Fund. Mr. Hamlin 
                      has managed the Fund since its inception in 1986. Prior to
                      joining Vanguard, Mr. Hamlin managed tax-exempt money     
                      market funds for a major investment company.              
                                                                                
                    The Fixed Income Group manages the investment and           
                    reinvestment of the assets of the Fund and continuously     
                    reviews, supervises and administers the Fund's              
                    
                    
                    
                    
    

14
<PAGE>

                    investment program, subject to the maturity and quality
                    standards specified in this Prospectus and supplemental
                    guidelines approved by the Fund's Board of Trustees. The
                    Fixed Income Group's selection of investments is based on:
                    (a) continuing credit analysis of those instruments held in
                    the Fund and those being considered for inclusion therein;
                    (b) possible disparities in yield relationships between
                    different fixed-income securities; and (c) actual or
                    anticipated movements in the general level of interest
                    rates.

                    Vanguard's Fixed Income Group places all orders for
                    purchases and sales of portfolio securities. Purchases of
                    portfolio securities are made either directly from the
                    issuer or from municipal securities dealers. The Fixed
                    Income Group may sell portfolio securities prior to their
                    maturity if circumstances and considerations warrant and if
                    it believes such dispositions advisable. The Fixed Income
                    Group seeks to obtain the best available net price and most
                    favorable execution for all portfolio transactions. ..

- --------------------------------------------------------------------------------
DIVIDENDS, 
CAPITAL GAINS
AND TAXES           Dividends consisting of virtually all of the ordinary income
                    of the Fund are declared daily and are payable to           
The Fund pays       shareholders of record at the close of the previous business
month-end           day. Such dividends are paid on the first business day of   
dividends           each month. Net capital gains distributions, if any, will be
                    made annually.                                              
                                                                                
                    Dividend and capital gains distributions may be             
                    automatically reinvested or received in cash. See "Choosing 
                    a Distribution Option" for a description of these           
                    distribution methods.                                       
                                                                                
                    In addition, in order to satisfy certain distribution       
                    requirements of the Tax Reform Act of 1986, the Fund may    
                    declare special year-end dividend and capital gains         
                    distributions during December. Such distributions, if       
                    received by shareholders by January 31, are deemed to have  
                    been paid by the Fund and received by shareholders by       
                    December 31 of the prior year.                           
                    
Dividends will be 
exempt from federal
and New York 
income taxes        The Fund intends to continue to qualify for taxation as a
                    "regulated investment company" under the Internal Revenue
                    Code so that it will not be subject to federal income tax to
                    the extent its income is distributed to shareholders. In
                    addition, the Fund intends to invest a sufficient portion of
                    its assets in municipal bonds and notes so that it will
                    continue to qualify to pay "exempt-interest dividends" to
                    shareholders. Such exempt-interest dividends are excluded
                    from a shareholder's gross income for federal tax purposes.
                    The Revenue Reconciliation Act enacted during 1993 provides
                    that market discount on tax-exempt bonds purchased after
                    April 30, 1993 must be taxed as ordinary income.
                    Accordingly, to the extent that the Fund purchases such
                    discounted securities, taxable income may result.
                    Furthermore, the Fund expects to invest substantially all of
                    its assets in New York municipal securities. As a result, it
                    will be eligible to pay to New York residents dividends that
                    will be exempt from New York State personal income taxes.
   
                    Net long-term capital gains realized by the Fund from the
                    sale of securities will be distributed as taxable capital
                    gains distributions for federal income tax purposes. Any
                    short-term capital gains or any taxable interest income will
    

                                                                             15

<PAGE>


   
                    be distributed as a taxable ordinary dividend distribution
                    for federal income tax purposes. In general, such taxable
                    income distributions from the Fund are expected to be
                    negligible in comparison with tax-exempt dividends. However,
                    under certain circumstances, the Fund may invest in
                    securities other than New York municipal obligations. In
                    such cases, a portion of the Fund's income may be subject to
                    New York income taxes, federal income taxes, or both.

                    At present, the Fund does not invest in AMT bonds. (See
                    "Investment Policies.") However, were the Fund to invest in
                    such bonds, all or a portion of the Fund's dividends, while
                    exempt from the regular federal income tax, would be a tax
                    preference item for purposes of the federal alternative
                    minimum tax.

A capital gain or loss 
may be realized upon
exchange or
redemption          A sale of the Fund's shares is a taxable event and may
                    result in a capital gain or loss. A capital gain or loss may
                    be realized from an ordinary redemption of shares, a
                    checkwriting redemption, or an exchange of shares between
                    two mutual funds (or two portfolios of a mutual fund). In
                    addition, if you held shares in the Fund for six months or
                    less, any capital loss realized upon redemption is
                    disallowed to the extent of the tax-exempt dividend income
                    you received.

                    Capital gains distributions from the Fund and any capital
                    gains or losses realized from the sale or exchange of shares
                    will generally be subject to state and local taxes.
    
                    The Fund is required to withhold 31% of any taxable
                    dividends, capital gains distributions, and redemptions paid
                    to shareholders who have not complied with IRS taxpayer
                    identification regulations. You may avoid this withholding
                    requirement by indicating your proper Social Security or
                    Taxpayer Identification Number on your Account Registration
                    Form and by certifying that you are not subject to backup
                    withholding.

                    Up to 85% of an individual's Social Security benefits may be
                    subject to federal income tax. Along with other factors,
                    total tax-exempt income, including any tax-exempt dividend
                    income from the Fund, is used to calculate the taxable
                    portion of Social Security benefits.

                    The Fund is organized as a Pennsylvania business trust and,
                    in the opinion of counsel, is not liable for any income or
                    franchise tax in the Commonwealth of Pennsylvania. The Fund
                    will be subject to Pennsylvania county personal property tax
                    in the county which is the site of its principal office.

                    The tax discussion set forth above is included for general
                    information only. Prospective investors should consult their
                    own tax advisers concerning the tax consequences of an
                    investment in the Fund.

- --------------------------------------------------------------------------------
   
THE SHARE PRICE 
OF THE FUND         The share price or "net asset value" per share of the Fund
                    is determined daily by dividing the total value of the
                    investments and other assets of the Fund, less any
                    liabilities, by the total outstanding shares of the Fund.
                    The net asset value per share of the Fund is determined as
                    of the close of regular trading on The New York Stock
                    Exchange (generally 4:00 p.m. Eastern time) on each day the
                    Exchange is open.
    

16
<PAGE>


                    When approved by the Board of Trustees, bonds and other
                    fixed-income securities of the Fund may be valued on the
                    basis of prices provided by a pricing service when such
                    prices are believed to reflect the fair market value of such
                    securities. (The prices provided by pricing services are
                    generally determined without regard to bid or last sale
                    prices. Because of the large number of outstanding municipal
                    bonds, the majority of issues do not trade each day;
                    therefore, last sale prices are not normally available. In
                    valuing such securities, the pricing services generally take
                    into account institutional size trading in similar groups of
                    securities and any developments related to specific
                    securities.) The methods used by the pricing service and the
                    valuations so established are reviewed by the Officers of
                    the Fund under the general supervision of the Trustees.
                    There are a number of pricing services available and the
                    Trustees, on the basis of ongoing evaluation of these
                    services, may use other pricing services or discontinue the
                    use of any pricing service.

                    Securities not priced in this manner are priced at the most
                    recent quoted bid price provided by investment dealers.
                    Short-term instruments maturing within 60 days of the
                    valuation date may be valued at cost, plus or minus any
                    amortized discount or premium. Other assets and securities
                    for which no quotations are readily available will be valued
                    in good faith at their fair value using methods determined
                    by the Trustees.
    
                    The price per share of the Fund can be found daily in the
                    mutual fund section of most major newspapers under the
                    heading of Vanguard.
    
- --------------------------------------------------------------------------------
GENERAL 
INFORMATION         Vanguard New York Insured Tax-Free Fund is a Pennsylvania
                    business trust. The Declaration of Trust permits the
                    Trustees to issue an unlimited number of shares of
                    beneficial interest, without par value, from an unlimited
                    number of classes of shares. Currently the Fund is offering
                    one class of shares.

                    Shares of the Fund when issued are fully paid and
                    non-assessable; participate equally in dividends,
                    distributions and net assets; are entitled to one vote per
                    share; have pro rata liquidation rights; and do not have
                    pre-emptive rights. Also, shares of the Fund have
                    non-cumulative voting rights, meaning that the holders of
                    more than 50% of the shares voting for the election of the
                    Trustees can elect all of the Trustees if they so choose.

                    Annual meetings of shareholders will not be held except as
                    required by the Investment Company Act of 1940 and other
                    applicable law. An annual meeting will be held to vote on
                    the removal of a Trustee or Trustees of the Fund if
                    requested in writing by the holders of not less than 10% of
                    the outstanding shares of the Fund.

                    All securities and cash are held by CoreStates Bank, N.A.,
                    Philadelphia, PA. The Vanguard Group, Inc., Valley Forge,
                    PA, serves as the Fund's Transfer and Dividend Disbursing
                    Agent. Price Waterhouse LLP serves as independent
                    accountants for the Fund and audits its financial statements
                    annually. The Fund is not involved in any litigation. 

- --------------------------------------------------------------------------------

                                                                              17

<PAGE>
                               SHAREHOLDER GUIDE

   
OPENING AN
ACCOUNT AND
PURCHASING
SHARES              To open a new account, either by mail or by wire, simply
                    complete and return an Account Registration Form and any
                    required legal documentation. Please indicate the amount you
                    wish to invest. Your purchase must be equal to or greater
                    than the $3,000 minimum initial investment requirement
                    ($1,000 for Uniform Gifts/ Transfers to Minors Act
                    accounts). In addition, you must be a New York resident to
                    invest in the Fund. If you need assistance with the Account
                    Registration Form or have any questions about this Fund,
                    please call our Investor Information Department at
                    1-800-662-7447. Note: For other types of registrations (e.g.
                    corporations, associations, other organizations, trusts or
                    powers of attorney), please call us to determine which
                    additional forms you may need.

                    The Fund's shares generally are purchased at the
                    next-determined net asset value after your investment has
                    been received in the form of Federal Funds. See "When Your
                    Account Will Be Credited". The Fund is offered on a no-load
                    basis (i.e., there are no sales commissions or 12b-1 fees).


Purchase 
Restrictions        1) Because of the risks associated with bond investments,
                       the Fund is intended to be a long-term investment vehicle
                       and is not designed to provide investors with a means of
                       speculating on short-term market movements. Consequently,
                       the Fund reserves the right to reject any specific
                       purchase (and exchange purchase) request. The Fund also
                       reserves the right to suspend the offering of shares for
                       a period of time.
    
                    2) Vanguard will not accept third-party period of time.
                       checks to purchase shares of the Fund. Please be sure
                       your purchase check is made payable to the Vanguard
                       Group.

Additional 
Investments         Subsequent investments may be made by mail ($100 minimum per
                    portfolio), wire ($1,000 minimum per portfolio), exchange
                    from another Vanguard Fund account ($100 minimum), or
                    Vanguard Fund Express.
                    ------------------------------------------------------------
<TABLE>
<CAPTION>
<S>                       <C>                              <C>  

                                                               ADDITIONAL INVESTMENTS 
                              NEW ACCOUNT                       TO EXISTING ACCOUNTS  
Purchasing By Mail        Please include the amount of       Additional investments should    
Complete and sign the     your initial investment on the     include the Invest-by-Mail       
enclosed Account          registration form, make your       remittance form attached to      
Registration Form         check payable to The Vanguard      your Fund confirmation                       
                          Group-76, and mail to:             statements. Please make your     
                                                             check payable to The Vanguard    
                                                             Group-76, write your account     
                                                             number on your check and,        
                          Vanguard Financial Center          using the return envelope        
                          P.O. Box 2600                      provided, mail to the address    
                          Valley Forge, PA 19482             indicated on the                 
                                                             Invest-by-Mail Form.     

                                 
For express or           Vanguard Financial Center           All written requests should be
registered mail,         455 Devon Park Drive                mailed to one of the addresses
send to:                 Wayne, PA 19087                     indicated for new accounts. Do
                                                             not send registered or express
                                                             mail to the post office box   
                                                             address.                      
                                                             
</TABLE>
- --------------------------------------------------------------------------------
18

<PAGE>
   
Purchasing By Wire                 CORESTATES BANK, N.A.                   
Money should be                    ABA 031000011                           
wired to:                          CORESTATES NO. 0141 1274                
                                   ATTN VANGUARD                           
Before Wiring                      VANGUARD NEW YORK INSURED TAX-FREE FUND 
Please contact                     ACCOUNT NUMBER                          
Client Services                    ACCOUNT REGISTRATION                    
(1-800-662-2739)                                                           
    
                    To assure proper receipt, please be sure your bank includes
                    the name of the Fund, the account number Vanguard has
                    assigned to you and the eight-digit CoreStates number. If
                    you are opening a new account, please complete the Account
                    Registration Form and mail it to the "New Account" address
                    after completing your wire arrangement. Note: Federal Funds
                    wire purchase orders will be accepted only when the Fund and
                    Custodian Bank are open for business.
                    -----------------------------------------------------------
 
Purchasing By
Exchange (from a
Vanguard account)   You may open an account or purchase additional shares of the
                    Fund by making an exchange from an existing Vanguard Fund
                    account. Accounts opened by exchange will have the same
                    registration as the existing account. Please note: the Fund
                    reserves the right to reject any exchange purchase request.
                    For more information, please call our Client Services
                    Department at 1-800-662-2739. Purchasing By Fund Express
Purchasing By       ------------------------------------------------------------
Fund Express

Special Purchase
and Automatic 
Investment          The Fund Express Special Purchase option lets you move money
                    from your bank account to your Vanguard account on an "as
                    needed" basis. Or if you choose the Automatic Investment
                    option, money will be moved automatically from your bank
                    account to your Vanguard account on the schedule (monthly,
                    bimonthly [every other month], quarterly or yearly) you
                    select. To establish these Fund Express options, please
                    provide the appropriate information on the Account
                    Registration Form. We will send you a confirmation of your
                    Fund Express service; please wait three weeks before using
                    the service.
- --------------------------------------------------------------------------------
CHOOSING A 
DISTRIBUTION
OPTION              You must select one of three distribution options:

                    1. Automatic Reinvestment Option--Both dividends and capital
                       gains distributions will be reinvested to purchase
                       additional Fund shares. This option will be selected for
                       you automatically unless you specify one of the other
                       options.
                    2. Cash Dividend Option--Your dividends will be paid in cash
                       and your capital gains will be reinvested in additional
                       Fund shares.

                    3. All Cash Option--Both dividend and capital gains
                       distributions will be paid in cash.

                    You may change your option by calling our Client Services
                    Department (1-800- 662-2739).

                    In addition, an option to reinvest your cash dividends
                    and/or capital gains distributions in another Vanguard Fund
                    account is available. Please call our Client Services
                    Department (1-800-662-2739) for information. You may also


                                                                              19



<PAGE>

                    elect Vanguard Dividend Express which allows you to
                    transfer your cash dividends and/or capital gains
                    distributions automatically to your bank account. Please see
                    "Other Vanguard Services" for more information.
- --------------------------------------------------------------------------------
    
TAX CAUTION         Under federal tax laws, the Fund is required to distribute  
                    net capital gains and investment income to Fund             
                    shareholders. These distributions are made to all           
Investors should    shareholders who own Fund shares as of the distribution's   
ask about the       record date, regardless of how long the shares have been    
timing of capital   owned. Purchasing shares just prior to the record date could
gains and dividend  have a significant impact on your tax liability for the     
distributions       year. For example, if you purchase shares immediately prior 
before investing    to the record date of a sizable capital gain, you will be   
                    assessed taxes on the amount of the capital gain            
                    distribution later paid even though you owned the Fund      
                    shares for just a short period of time. (Taxes are due on   
                    the distributions even if the capital gain is reinvested in 
                    additional Fund shares.) While the total value of your      
                    investment will be the same after the capital gain          
                    distribution--the amount of the capital gain distribution   
                    will offset the drop in the net asset value of the          
                    shares--you should be aware of the tax implications the     
                    timing of your purchase may have.                           
                                                                                
                    Prospective investors should, therefore, inquire about      
                    potential distributions before investing. The Fund's annual 
                    capital gains distribution normally occurs in December,     
                    while income dividends are generally paid on the first      
                    business day of each month. For additional information on   
                    distributions and taxes, see the section titled "Dividends, 
                    Capital Gains, and Taxes."                                  
                    
                    

                    
- --------------------------------------------------------------------------------
IMPORTANT
INFORMATION         The easiest way to establish optional Vanguard services on  
                    your account is to select the options you desire when you   
Establishing        complete your Account Registration Form. If you wish to add 
Optional            shareholder options later, you may need to provide Vanguard 
Services            with additional information and a signature guarantee.      
                    Please call our Client Services Department (1-800-662-2739) 
                    for further assistance.                              

Signature 
Guarantees          For our mutual protection, we may require a signature
                    guarantee on certain written transaction requests. A
                    signature guarantee verifies the authenticity of your
                    signature, and may be obtained from banks, brokers and any
                    other guarantor that Vanguard deems acceptable. A signature
                    guarantee cannot be provided by a notary public.


Certificates        Share certificates will be issued upon request. If a
                    certificate is lost, you may incur an expense to replace it.

Broker-Dealer 
Purchases           If you purchase shares in Vanguard Funds through a
                    registered broker-dealer or investment adviser the
                    broker-dealer or adviser may charge a service fee.


Cancelling
Trades              The Fund will not cancel any trade (e.g., a purchase,
                    exchange or redemption) believed to be authentic, received
                    in writing or by telephone, once the trade request has been
                    received.

20
<PAGE>

Electronic
Prospectus
Delivery            If you would prefer to receive a prospectus for the Fund or
                    any of the Vanguard Funds in an electronic format, please
                    call 1-800-231-7870 for additional information. If you elect
                    to do so, you may also receive a paper copy of the
                    prospectus, by calling 1-800-662-7447.
- --------------------------------------------------------------------------------
WHEN YOUR
ACCOUNT WILL
BE CREDITED         The trade date is the date on which your account is
                    credited. It is generally the day on which the Fund receives
                    your investment in the form of Federal Funds (monies
                    credited to the Fund's Custodian Bank by a Federal Reserve
                    Bank). Your trade date varies according to your method of
                    payment for your shares.
   
                    Purchases of Fund shares by check will receive a trade date
                    the day the funds are received in good order by Vanguard.
                    Thus, if your purchase by check is received by the close of
                    regular trading on the New York Stock Exchange (generally
                    4:00 p.m. Eastern time), your trade date is the business day
                    your check is received in good order. If your purchase is
                    received after the close of the Exchange, your trade date is
                    the business day following receipt of your check.
    
                    For purchases by Federal Funds wire or exchange, the Fund is
                    credited immediately with Federal Funds. Thus, if your
                    purchase by Federal Funds wire or exchange is received by
                    the close of the Exchange, your trade date is the day of
                    receipt. If your purchase is received after the close of the
                    Exchange, your trade date is the business day following
                    receipt of your wire or exchange.

                    Your shares are purchased at the net asset value determined
                    on your trade date. You will begin to earn dividends on the
                    calendar day following the trade date. (For a Friday trade
                    date, you will begin earning dividends on Saturday.)

                    In order to prevent lengthy processing delays caused by the
                    clearing of foreign checks, Vanguard will only accept a
                    foreign check which has been drawn in U.S. dollars and has
                    been issued by a foreign bank with a U.S. correspondent
                    bank. The name of the U.S. correspondent bank must be
                    printed on the face of the foreign check. ..

- --------------------------------------------------------------------------------
   
SELLING YOUR 
SHARES              You may withdraw any portion of the funds in your account by
                    redeeming shares at any time. You generally may initiate a
                    request by writing or by telephoning. Your redemption
                    proceeds are normally mailed, credited or wired--depending
                    upon the method of withdrawal you have previously
                    chosen--within two business days after the receipt of the
                    request in Good Order.
    

Selling By Writing
a Check             You may withdraw funds from your account by writing a check
                    payable in the amount of $250 or more. When a check is
                    presented for payment to the Fund's agent, CoreStates Bank,
                    the Fund will redeem sufficient shares in your account at
                    the net asset value next determined to cover the amount of
                    the check.

                    In order to establish the checkwriting option on your
                    account, all registered shareholders must sign a signature
                    card. After your completed signature card is received by the
                    Fund, an initial supply of checks will be mailed within 10
                    business days. There is no charge for checks or for their

                                                                              21
<PAGE>

                    clearance. Corporations, trusts and other organizations
                    should call our Client Services Department (1-800-662-2739)
                    before submitting signature cards, as additional documents
                    may be required to establish the checkwriting service.

                    Before establishing the checkwriting option, you should be
                    aware that:

                    1. Writing a check (a redemption of shares) is a taxable
                       event.

                    2. The Fund does not allow an account to be closed through
                       the checkwriting option.

                    3. Vanguard cannot guarantee a stop payment on any check. If
                       you wish to reverse a stop payment order, you must do so 
                       in writing.

                    4. Shares held in certificate form cannot be redeemed using
                       the checkwriting option.

                    5. The Fund reserves the right to terminate or alter this
                       service at any time.
                    ------------------------------------------------------------
Selling By Mail     Requests should be mailed to Vanguard Financial Center,
                    Vanguard New York Insured Tax-Free Fund, P.O. Box 1120,
                    Valley Forge, PA 19482. (For express or registered mail,
                    send your request to Vanguard Financial Center, Vanguard New
                    York Insured Tax-Free Fund, 455 Devon Park Drive, Wayne, PA
                    19087.)

                    The redemption price of shares will be the Fund's net asset
                    value next determined after Vanguard has received all
                    required documents in Good Order.
                    ------------------------------------------------------------
Definition of
Good Order          Good Order means that the request includes the following:

                    1. The account number and Fund name.
 
                    2. The amount of the transaction (specified in dollars or
                       shares).

                    3. Signatures of all owners exactly as they are registered
                       on the account.

                    4. Any required signature guarantees.

                    5. Other supporting legal documentation that might be
                       required, in the case of estates, corporations, trusts, 
                       and certain other accounts.

                    6. Any certificates that you hold for the account.

                    If you have questions about this definition as it pertains
                    to your request, please call our Client Services Department
                    at 1-800-662-2739.
                    ------------------------------------------------------------
Selling By 
Telephone           To sell shares by telephone, you or your pre-authorized
                    representative may call our Client Services Department at
                    1-800-662-2739. For telephone redemptions, you may have the
                    proceeds sent to you either by mail or by wire. In addition
                    to the details below, please see "Important Information
                    About Telephone Transactions."
   
                    By Mail: Telephone mail redemption is automatically
                    established on your account unless you indicate otherwise on
                    your Account Registration Form. You may redeem any amount by
                    calling Vanguard. The proceeds will be paid to the
                    registered shareholders and mailed to the address of record.
                    Please Note: As a protection against fraud, your telephone
                    mail redemption privilege will be suspended for 10 calendar
    




22

<PAGE>

   
                    days following any expedited address change to your account.
                    An expedited address change is one that is made by
                    telephone, by Vanguard Online or, in writing, without the
                    signatures of all account owners.
    
                    By Wire: Telephone wire redemption must be specifically
                    elected for your account. The best time to elect telephone
                    wire redemption is at the time you complete your Account
                    Registration Form. If you do not presently have telephone
                    wire redemption and wish to establish it, please contact our
                    Client Services Department.

                    With the wire redemption option, you may withdraw a minimum
                    of $1,000 and have the amount wired directly to your bank
                    account. Wire redemptions less than $5,000 are subject to a
                    $5 charge deducted by Vanguard. There is no Vanguard charge
                    for wire redemptions of $5,000 or more. However, your bank
                    may assess a separate fee to accept incoming wires.

                    A request to change the bank associated with your wire
                    redemption option must be received in writing, signed by
                    each registered shareholder, and accompanied by a voided
                    check or preprinted deposit slip. A signature guarantee is
                    required if your bank registration is not identical to your
                    Vanguard Fund account registration.
                    ------------------------------------------------------------
Selling By Fund
Express             If you select the Fund Express Automatic Withdrawal option,
                    money will be automatically moved from your Vanguard Fund 
Automatic           account to your bank account according to the schedule you 
Withdrawal          have selected. The Special Redemption option lets you move 
& Special           money from your Vanguard account to your bank account on an
Redemption          "as needed" basis. To establish these Fund Express options,
                    please provide the appropriate information on the Account  
                    Registration Form. We will send you a confirmation of your 
                    Fund Express service; please wait three weeks before using 
                    the service.                                               
       
                    ------------------------------------------------------------
Selling By Exchange You may sell shares of the Fund by making an exchange to
                    another Vanguard Fund account. Please see "Exchanging Your
                    Shares" for details.
                    ------------------------------------------------------------
Important
Redemption
Information         Shares purchased by check or Fund Express may be redeemed at
                    any time. However, your redemption proceeds will not be paid
                    until payment for the purchase is collected, which may take
                    up to ten calendar days.

Delivery of
Redemption
Proceeds            Redemption requests received by telephone prior to the close
                    of regular trading on the New York Stock Exchange (generally
                    4:00 p.m. Eastern time) are processed on the business day of
                    receipt and the redemption proceeds are normally sent on the
                    following business day.

                    Redemption requests received by telephone after the close of
                    the Exchange are processed on the business day following
                    receipt and the proceeds are normally sent on the second
                    business day following receipt.
   
                    Redemption proceeds must be sent to you within seven days of
                    receipt of your request in Good Order except as described
                    above in "Important Redemption Information."
    
                                                                              23


<PAGE>
                    If you experience difficulty in making a telephone
                    redemption during periods of drastic economic or market
                    changes, your redemption request may be made by regular or
                    express mail. It will be implemented at the net asset value
                    next determined after your request has been received by
                    Vanguard in Good Order. The Fund reserves the right to
                    revise or terminate the telephone redemption privilege at
                    any time.

                    The Fund may suspend the redemption right or postpone
                    payment at times when the New York Stock Exchange is closed
                    or under any emergency circumstances as determined by the
                    United States Securities and Exchange Commission.
                    -----------------------------------------------------------
   
Vanguard's Average
Cost Statement      If you make a redemption from a qualifying account, Vanguard
                    will send you an Average Cost Statement which provides you
                    with the tax basis of the shares you redeemed. Please see
                    "Statements and Reports" for additional information.
                    -----------------------------------------------------------
Low Balance Fee and 
Minimum Account
Balance 
Requirement         Due to the relatively high cost of maintaining smaller
                    accounts, the Fund will automatically deduct a $10 annual
                    fee from accounts with balances falling below $2,500 ($1,000
                    for Uniform Gifts/Transfers to Minors Act accounts). This
                    fee deduction will occur mid-year, beginning in 1996. The
                    fee generally will be waived for investors whose aggregate
                    Vanguard assets exceed $50,000.

                    In addition, the Fund reserves the right to liquidate any
                    non-retirement account that is below the minimum initial
                    investment amount of $3,000. If at any time the total
                    investment does not have a value of at least $3,000, you may
                    be notified that your account is below the Fund's minimum
                    account balance requirement. You would then be allowed 60
                    days to make an additional investment before the account is
                    liquidated. Proceeds would be promptly paid to the
                    registered shareholder.

                    Vanguard will not liquidate your account if it has fallen
                    below $3,000 solely as a result of declining markets (i.e.,
                    a decline in a Fund's net asset value).
    
- --------------------------------------------------------------------------------
EXCHANGING 
YOUR SHARES         Should your investment goals change, you may exchange your
                    shares of Vanguard New York Insured Tax-Free Fund for those
                    of other available Vanguard Funds.

Exchanging By 
Telephone           When exchanging shares by telephone, please have ready the  
                    Fund name, account number, Social Security Number or    
Call Client         Employer Identification Number listed on the account, and   
Services            the exact name and address in which the account is          
(1-800-662-2739)    registered. Only the registered shareholder may complete    
                    such an exchange. Requests for telephone exchanges received 
                    prior to the close of trading on the New York Stock Exchange
                    (generally 4:00 p.m. Eastern time) are processed at the     
                    close of business that same day. Requests received after the
                    close of the Exchange are processed the next business day.  
                    Telephone exchanges are not accepted into or from Vanguard  
                    Balanced Index, Vanguard Index Trust, Vanguard International
                    Equity Index Fund, and Vanguard Quantitative Portfolios. If 
                    
                    

24
<PAGE>

                    you experience difficulty in making a telephone exchange,
                    your exchange request may be made by regular or express
                    mail, and it will be implemented at the closing net asset
                    value on the date received by Vanguard provided the request
                    is received in Good Order.
                    ------------------------------------------------------------
Exchanging By Mail  Please be sure to include on your exchange request the name
                    and account number of your current Fund, the name of the
                    Fund you wish to exchange into, the amount you wish to
                    exchange, and the signatures of all registered account
                    holders. Send your request to Vanguard Financial Center,
                    Vanguard New York Insured Tax-Free Fund, P.O. Box 1120,
                    Valley Forge, PA 19482. (For express or registered mail,
                    send your request to Vanguard Financial Center, Vanguard New
                    York Insured Tax-Free Fund, 455 Devon Park Drive, Wayne, PA
                    19087.)
                    ------------------------------------------------------------
Important Exchange
Information         Before you make an exchange, you should consider the
                    following:

                    o Please read the Fund's prospectus before making an
                      exchange. For a copy and for answers to any questions you
                      may have, call our Investor Information Department
                      (1-800-662-7447).

                    o An exchange is treated as a redemption and a purchase.
                      Therefore, you could realize a taxable gain or loss on the
                      transaction.

                    o Exchanges are accepted only if the registrations and the
                      Taxpayer Identification numbers of the two accounts are
                      identical.

                    o The shares to be exchanged must be on deposit and not held
                      in certificate form.

                    o New accounts are not currently accepted in
                      Vanguard/Windsor Fund or Vanguard/PRIMECAP Fund.

                    o The redemption price of shares redeemed by exchange is the
                      net asset value next determined after Vanguard has 
                      received the required documentation in Good Order.

                    o When opening a new account by exchange, you must meet the
                      minimum investment requirement of the new Fund.

                    Every effort will be made to maintain the exchange
                    privilege. However, the Fund reserves the right to revise or
                    terminate its provisions, limit the amount of or reject any
                    exchange, as deemed necessary, at any time.

                    The Fund's exchange privilege is only available in New York,
                    the only state in which the Fund's shares are registered for
                    sale.

- --------------------------------------------------------------------------------
EXCHANGE 
PRIVILEGE
LIMITATIONS         The Fund's exchange privilege is not intended to afford
                    shareholders a way to speculate on short-term movements in
                    the market. Accordingly, in order to prevent excessive use
                    of the exchange privilege that may potentially disrupt the
                    management of the Fund and increase transaction costs, the
                    Fund has established a policy of limiting excessive exchange
                    activity.


                                                                              25

<PAGE>

   
                    Exchange activity generally will not be deemed excessive if
                    limited to two substantive exchange redemptions (at least 30
                    days apart) from the Fund during any twelve-month period.
                    Notwithstanding these limitations, the Fund reserves the
                    right to reject any purchase request (including exchange
                    purchases from other Vanguard portfolios) that is reasonably
                    deemed to be disruptive to efficient portfolio management.
    
- --------------------------------------------------------------------------------
IMPORTANT 
INFORMATION
ABOUT TELEPHONE
TRANSACTIONS        The ability to initiate redemptions (except wire
                    redemptions) and exchanges by telephone is automatically
                    established on your account unless you request in writing
                    that telephone transactions on your account not be
                    permitted. The ability to initiate wire redemptions by
                    telephone will be established on your account only if you
                    specifically elect this option in writing.

                    To protect your account from losses resulting from
                    unauthorized or fraudulent telephone instructions, Vanguard
                    adheres to the following security procedures:

                    1. Security Check. To request a transaction by telephone,
                    the caller must know (i) the name of the Fund; (ii) the
                    10-digit account number; (iii) the exact name and address
                    used in the registration; and (iv) the Social Security or
                    Employer Identification number listed on the account.

                    2. Payment Policy. The proceeds of any telephone redemption
                    made by mail will be made payable to the registered
                    shareowner and mailed to the address of record, only. In the
                    case of a telephone redemption by wire, the wire transfer
                    will be made only in accordance with the shareowner's prior
                    written instructions.

   
                    Neither the Fund nor Vanguard will be responsible for the
                    authenticity of transaction instructions received by
                    telephone, provided that reasonable security procedures have
                    been followed. Vanguard believes that the security
                    procedures described above are reasonable, and that if such
                    procedures are followed, you will bear the risk of any
                    losses resulting from unauthorized or fraudulent telephone
                    transactions on your account. If Vanguard fails to follow
                    reasonable security procedures, it may be liable for any
                    losses resulting from unauthorized or fraudulent telephone
                    transactions on your account.
    
- --------------------------------------------------------------------------------
TRANSFERRING
REGISTRATION        You may transfer the registration of any of your Fund shares
                    to another person by completing a transfer form and sending
                    it to: Vanguard Financial Center, P.O. Box 1110, Valley
                    Forge, PA 19482, Attention: Transfer Department. The request
                    must be in Good Order. Before mailing your request, please
                    call our Client Services Department (1-800-662-2739) for
                    full instructions.
- --------------------------------------------------------------------------------
STATEMENTS AND 
REPORTS             Vanguard will send you a confirmation statement each time
                    you initiate a transaction in your account except for
                    checkwriting redemptions from Vanguard money market
                    accounts. You will also receive a comprehensive account
                    statement at the end of each calendar quarter. The
                    fourth-quarter statement will be a year-end statement,
                    listing all transaction activity for the entire calendar
                    year.

                    Vanguard's Average Cost Statement provides you with the
                    average cost of shares redeemed from your account, using the
                    average cost single category method. This service is

26

<PAGE>

   
                    available for most taxable accounts opened since January 1,
                    1986. In general, investors who redeemed shares from a
                    qualifying Vanguard account may expect to receive their
                    Average Cost Statement along with their Fund Summary
                    Statement. Please call our Client Services Department
                    (1-800-662-2739) for information.
     
                    Financial reports on the Fund will be mailed to you
                    semi-annually, according to the Fund's fiscal year-end. ..
- --------------------------------------------------------------------------------
OTHER VANGUARD 
SERVICES            For more information about any of these services, please
                    call our Investor Information Department at 1-800-662-7447.

Vanguard
Direct Deposit
Service             With Vanguard's Direct Deposit Service, most U.S. Government
                    checks (including Social Security and military pension
                    checks) and private payroll checks may be automatically
                    deposited into your Vanguard Fund account. Separate
                    brochures and forms are available for direct deposit of U.S.
                    Government and private payroll checks.


Vanguard Automatic
Exchange Service    Vanguard's Automatic Exchange Service allows you to move
                    money automatically among your Vanguard Fund accounts. For
                    instance, the service can be used to "dollar cost average"
                    from a money market portfolio into a stock or bond fund or
                    to contribute to an IRA or other retirement plan. Please
                    contact our Client Services Department at 1-800-662-2739 for
                    additional information.

Vanguard Fund
Express             Vanguard's Fund Express allows you to transfer money between
                    your Fund account and your account at a bank, savings and
                    loan association, or a credit union that is a member of the
                    Automated Clearing House (ACH) system. You may elect this
                    service on the Account Registration Form or call our
                    Investor Information Department (1-800-662-7447) for a Fund
                    Express application.
                    
                    Special rules govern how your Fund Express purchases or
                    redemptions are credited to your account. In addition, some
                    services of Fund Express cannot be used with specific
                    Vanguard Funds. For more information, please refer to the
                    Vanguard Fund Express brochure.

Vanguard
Dividend 
Express             Vanguard's Dividend Express allows you to transfer your
                    dividends and/or capital gains distributions automatically
                    from your Fund account, one business day after the Fund's
                    payable date, to your account at a bank, savings and loan
                    association, or a credit union that is a member of the
                    Automated Clearing House (ACH) system. You may elect this
                    service on the Account Registration Form or call our
                    Investor Information Department (1-800-662-7447) for a
                    Vanguard Dividend Express application.

Vanguard
Tele-Account        Vanguard's Tele-Account is a convenient, automated service
                    that provides share price, price change and yield quotations
                    on Vanguard Funds through any TouchTone(TR) telephone. This
                    service also lets you obtain information about your account
                    balance, your last transaction, and your most recent
                    dividend or capital gains payment. To contact Vanguard's
                    Tele-Account service, dial 1-800-ON- BOARD (1-800-662-6273).
                    A brochure offering detailed operating instructions is
                    available from our Investor Information Department
                    (1-800-662-7447).
- --------------------------------------------------------------------------------
                                                                              27



<PAGE>

  







 
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<PAGE>
   Vanguard
   NEW YORK
   INSURED
TAX-FREE FUND
 
The Vanguard Group 
 of Investment 
 Companies 
Vanguard Financial Center 
P.O. Box 2600 
Valley Forge, PA 19482 
  
Investor Information 
 Department: 
1-800-662-7447 (SHIP) 
  
Client Services 
 Department: 
1-800-662-2739 (CREW) 
  
Tele-Account for 
 24-Hour Access: 
1-800-662-6273 (ON-BOARD) 
  
Telecommunication 
 Service for the 
 Hearing-Impaired: 
1-800-662-2738 
  
Transfer Agent: 
The Vanguard Group, Inc. 
Vanguard Financial Center 
Valley Forge, PA 19482 
 
P076 

  

 
                                                            
   Vanguard
   NEW YORK
   INSURED
TAX-FREE FUND



 
P R O S P E C T U S 

  MARCH 29, 1996
 


    A member of
 THE VANGUARD GROUP.

<PAGE>

                                    PART B 
 
                   VANGUARD NEW YORK INSURED TAX-FREE FUND 
 
   
                     STATEMENT OF ADDITIONAL INFORMATION 
                                MARCH 29, 1996 

   This Statement is not a prospectus but should be read in conjunction with 
the Fund's current Prospectus dated March 29, 1996. To obtain this 
Prospectus, please call: 
    

                  Vanguard's Investor Information Department 
                                1-800-662-7447 


                              TABLE OF CONTENTS 


   
                                                                    Page 
                                                                  -------- 
Investment Limitations  .......................................      B-1 
Investment Policies  ..........................................      B-2 
Risks Factors  ................................................      B-6 
Yield and Total Return  .......................................      B-7 
Performance Measures  .........................................      B-7 
Investment Management  ........................................      B-9 
Purchase of Shares  ...........................................      B-9 
Redemption of Shares  .........................................      B-9 
Management of the Fund  .......................................     B-11 
Description of Shares and Voting Rights  ......................     B-14 
Financial Statements  .........................................     B-15 
Appendix A--Description of Municipal Bonds and their Ratings  .     B-16 
Appendix B--Municipal Lease Obligations  ......................     B-19 
    

  


                            INVESTMENT LIMITATIONS 

   The following limitations cannot be changed without the consent of the 
holders of a majority of the Fund's outstanding shares (as defined in the 
Investment Company Act of 1940 (the "1940 Act").

       1. The Fund will not invest in securities other than municipal bonds, 
   except that it may make temporary investments in (a) notes issued by or on 
   behalf of municipal or corporate issuers, obligations of the United States 
   Government and its agencies or instrumentalities, commercial paper and 
   bank certificates of deposit; (b) any investment companies investing in 
   such securities which have investment objectives and policies consistent 
   with those of the Fund, to the extent permitted by the 1940 Act; and (c) 
   any such securities or municipal bonds subject to short-term repurchase 
   agreements; 
   
       2. The Fund will limit the aggregate value of all issuers (except U.S. 
   Government and cash items, as defined under Subchapter M of the Internal 
   Revenue Code (the "Code"), each of which exceeds 5% of the Portfolio's 
   total assets, to an aggregate amount of 50% of such assets; 
    
       3. The Fund will limit the aggregate value of holdings of a single 
   issuer (except U.S. Government and cash items, as defined in the Code) to 
   a maximum of 25% of the Fund's total assets. For the purposes of this 
   limitation, identification of the issuer will be based on a determination 
   of the source of assets and revenues committed to meeting interest and 
   principal payments of each security; 
   
       4. The Fund will not borrow money except for temporary or emergency 
   purposes and then only in an amount not exceeding 10% of the value of the 
   total assets of that Fund. The Fund will repay all borrowing before making 
   additional investments. Interest paid on such borrowings will reduce 
   income; 
    


                                                                             B-1


<PAGE>

       5. The Fund will not pledge, mortgage or hypothecate its assets to any 
   extent greater than 10% of the value of the total assets of the Fund;
 
       6. The Fund will not issue senior securities as defined in the 1940 
   Act;
 
       7. The Fund will not engage in the business of underwriting any issue 
   of securities issued by other persons, except to the extent that it may 
   technically be deemed to be an underwriter under the Securities Act of 
   1933, as amended, in disposing of investment securities;
 
       8. The Fund will not purchase or sell real estate, but this shall not 
   prevent investments in municipal bonds secured by real estate or interests 
   therein;
 
       9. The Fund will not make loans to other persons, except by the 
   purchase of bonds, debentures or similar obligations which are publicly 
   distributed and as provided under "Lending of Securities";
 
       10. The Fund will not purchase on margin or sell short, except as 
   specified below in Investment Limitation No. 12;
 
       11. The Fund will not purchase or retain securities of an issuer if 
   those Trustees of the Fund, each of whom owns more than 1/2 of 1% of such 
   securities, together own more than 5% of the securities of such issuer;
 
       12. The Fund will not purchase or sell commodities or commodities 
   contracts, except that the Fund may invest in bond futures contracts, bond 
   options and options on bond futures contracts to the extent that not more 
   than 5% of the Fund's assets are required as deposit on futures contracts 
   and not more than 20% of the Fund's assets are invested in futures 
   contracts and/or options transactions at any time;
 
       13. The Fund will not invest in securities of other investment 
   companies except as they may be acquired as part of a merger, 
   consolidation or acquisition of assets or otherwise to the extent 
   permitted by Section 12 of the 1940 Act;
 
       14. The Fund will not invest in put, call, straddle or spread options 
   (except as described above in investment limitation No. 12) or interests 
   in oil, gas or other mineral exploration or development programs;
 
       15. The Fund will not purchase an industrial revenue bond if as a 
   result of such purchase (i) more than 5% of the Fund's total assets, 
   determined at market value at the time of the proposed investment, would 
   be invested in industrial revenue bonds where the payment of principal and 
   interest is the responsibility of a company with less than three (3) 
   years' operating history, or (ii) more than 20% of the Fund's total 
   assets, determined at market value at the time of the proposed investment, 
   would be invested in industrial development bonds. These restrictions do 
   not apply to municipal obligations where the payment of principal and 
   interest is the responsibility of a government or the political 
   subdivision of a government; and 
   
       16. The Fund will not purchase or otherwise acquire any security 
   (including the Fund's investment in The Vanguard Group, Inc.) if, as a 
   result, more than 15% of its net assets would be invested in securities 
   that are illiquid. 
    
   The above-mentioned investment limitations are considered at the time 
investment securities are purchased. Notwithstanding these limitations, the 
Fund may own all or any portion of the securities of, or make loans to, or 
contribute to the costs or other financial requirements of, any company which 
will be (1) wholly-owned by the Fund and one or more other investment 
companies and (2) primarily engaged in the business of providing, at cost, 
management, administrative, distribution and/or related services to the Fund 
and such other investment companies. Additionally, the Fund may invest in 
when-issued securities without limitation. Please see the Prospectus for a 
description of such securities. 


                             INVESTMENT POLICIES 

   Repurchase Agreements  The Fund may invest in repurchase agreements with
commercial banks, brokers or dealers either for defensive purposes due to market
conditions or to generate income from its excess cash balances. A repurchase

B-2
<PAGE>

agreement is an agreement under which the Fund acquires a money market
instrument (generally a security issued by the U.S. Government or an agency
thereof, a banker's acceptance or a certificate of deposit) from a commercial
bank, broker or dealer, subject to resale to the seller at an agreed upon price
and date (normally, the next business day). A repurchase agreement may be
considered a loan collateralized by securities. The resale price reflects an
agreed upon interest rate effective for the period the instrument is held by the
Fund and is unrelated to the interest rate on the underlying instrument. In
these transactions, the securities acquired by the Fund (including accrued
interest earned thereon) must have a total value in excess of the value of the
repurchase agreement and are held by the Fund's custodian bank until
repurchased. In addition, the Fund's Board of Trustees will monitor the Fund's
repurchase agreement transactions generally and will establish guidelines and
standards for review by the investment adviser of the creditworthiness of any
bank, broker or dealer party to a repurchase agreement with the Fund. No more
than an aggregate of 15% of a Fund's assets, at the time of investment, will be
invested in repurchase agreements having maturities longer than seven days and
securities subject to legal or contractual restrictions on resale, or for which
there are no readily available market quotations.

   The use of repurchase agreements involves certain risks. For example, if 
the other party to the agreement defaults on its obligations to repurchase 
the underlying security at a time when the value of the security has 
declined, the Fund may incur a loss upon disposition of the security. If the 
other party to an agreement becomes insolvent and subject to liquidation or 
reorganization under the Bankruptcy Code or other laws, a court may determine 
that the underlying security is collateral for a loan by the Fund not within 
the control of the Fund and therefore the realization by the Fund on such 
collateral may be automatically stayed. Finally, it is possible that the Fund 
may not be able to substantiate its interest in the underlying security and 
may be deemed an unsecured creditor of the other party to the agreement. 
While the Fund's management acknowledges these risks, it is expected that 
they can be controlled through careful monitoring procedures. 

   
   Lending of Securities  The Fund may lend its investment securities to 
qualified institutions who need to borrow securities in order to complete 
certain transactions, such as covering short sales, avoiding failures to 
deliver securities or completing arbitrage operations. By lending its 
investment securities, the Fund attempts to increase its income through the 
receipt of interest on the loan. Any gain or loss in the market price of the 
securities loaned that might occur during the term of the loan would be for 
the account of the Fund. The Fund may lend its investment securities to 
qualified brokers, dealers, banks or other financial institutions, so long as 
the terms and the structure of such loans are not inconsistent with the 1940 
Act, or the Rules and Regulations or interpretations of the Securities and 
Exchange Commission (the "Commission") thereunder, which currently require 
that (a) the borrower pledge and maintain with the Fund collateral having a 
value at all times not less than 100% of the value of the securities loaned, 
(b) the borrower add to such collateral whenever the price of the securities 
loaned rises (i.e., the borrower "marks to the market" on a daily basis), (c) 
the loan be made subject to termination by the Fund at any time and (d) the 
Fund receive reasonable interest on the loan (which may include the Fund 
investing any cash collateral in interest bearing short-term investments), 
any distribution on the loaned securities and any increase in their market 
value. The Fund will not lend its investment securities, if as a result, the 
aggregate of such loans exceeds 10% of the value of its total assets. Loan 
arrangements made by the Fund will comply with all other applicable 
regulatory requirements, including the rules of the New York Stock Exchange, 
which rules presently require the borrower, after notice, to redeliver the 
securities within the normal settlement time of three business days. All 
relevant facts and circumstances, including the creditworthiness of the 
broker, dealer or institution, will be considered in making decisions with 
respect to the lending of securities, subject to review by the Fund's Board 
of Trustees. Income derived from lending of securities is not tax-exempt, 
and, thus, the Fund will limit such activity in accordance with its 
investment objective. 
    

   Futures Contracts and Options  The Fund may enter into futures contracts,
options, and options on futures contracts for the purpose of simulating full
investment and reducing transactions costs. Futures contracts provide for the
future sale by one party and purchase by another party of a specified amount of
a specific security at a specified future time and at a specified price. Futures
contracts which are standardized as to maturity date and underlying financial

                                                                             B-3
<PAGE>

   
instrument are traded on national futures exchanges. Futures exchanges and
trading are regulated under the Commodity Exchange Act by the Commodity Futures
Trading Commission ("CFTC"), a U.S. Government Agency. Assets committed to
futures contracts will be segregated at the Fund's custodian bank to the extent
required by law.
    

   Although futures contracts by their terms call for actual delivery or 
acceptance of the underlying securities, in most cases the contracts are 
closed out before the settlement date without the making or taking of 
delivery. Closing out an open futures position is done by taking an opposite 
position ("buying" a contract which has previously been "sold," or "selling" 
a contract previously purchased) in an identical contract to terminate the 
position. Brokerage commissions are incurred when a futures contract is 
bought or sold. 

   Futures traders are required to make a good faith margin deposit in cash 
or government securities with a broker or custodian to initiate and maintain 
open positions in futures contracts. A margin deposit is intended to assure 
completion of the contract (delivery or acceptance of the underlying 
security) if it is not terminated prior to the specified delivery date. 
Minimal initial margin requirements are established by the futures exchange 
and may be changed. Brokers may establish deposit requirements which are 
higher than the exchange minimums. Futures contracts are customarily 
purchased and sold at prices which may range upward from less than 5% of the 
value of the contract being traded. 

   After a futures contract position is opened, the value of the contract is 
marked to market daily. If the futures contract price changes, to the extent 
that the margin on deposit does not satisfy margin requirements, payment of 
additional "variation" margin will be required. Conversely, changes in the 
contract value may reduce the required margin, resulting in a repayment of 
excess margin to the contract holder. Variation margin payments are made to 
and from the futures broker for as long as the contract remains open. The 
Fund expects to earn interest income on its margin deposits. 

   Traders in futures contracts may be broadly classified as either "hedgers" 
or "speculators." Hedgers use the futures markets primarily to offset 
unfavorable changes in the value of securities otherwise held for investment 
purposes or expected to be acquired by them. Speculators are less inclined to 
own the securities underlying the futures contracts which they trade, and use 
futures contracts with the expectation of realizing profits from fluctuations 
in the interest rates of underlying securities. The Fund intends to use 
futures contracts only for bona fide hedging purposes. 

   Regulations of the CFTC applicable to the Fund require that all of its 
futures transactions constitute bona fide hedging transactions. The Fund will 
only sell futures contracts to protect securities it owns against price 
declines or purchase contracts to protect against an increase in the price of 
securities it intends to purchase. As evidence of this hedging interest, the 
Fund expects that approximately 75% of its futures contract purchases will be 
"completed," that is, equivalent amounts of related securities will have been 
purchased or are being purchased by the Fund upon sale of open futures 
contracts. 

   Although techniques other than the sale and purchase of futures contracts 
could be used to control the Fund's exposure to market fluctuations, the use 
of futures contracts may be a more effective means of hedging this exposure. 
While the Fund will incur commission expenses in both opening and closing out 
futures positions, these costs are lower than transaction costs incurred in 
the purchase and sale of the underlying securities. 

   Restrictions on the Use of Futures Contracts  The Fund will not enter into 
futures contract transactions to the extent that, immediately thereafter, the 
sum of its initial margin deposits on open contracts exceeds 5% of the market 
value of the Fund's total assets. In addition, the Fund will not enter into 
futures contracts to the extent that its outstanding obligations to purchase 
securities under these contracts would exceed 20% of the Fund's total assets. 

   Risk Factors in Futures Transactions  Positions in futures contracts may be
closed out only on an Exchange which provides a secondary market for such
futures. However, there can be no assurance that a liquid secondary market will
exist for any particular futures contract at any specific time. Thus, it may not
be possible to close a futures position. In the event of adverse price
movements, the Fund would continue to be required to make daily cash payments to
maintain its required margin. In such situations, if the Fund has insufficient


B-4
<PAGE>

   
cash, it may have to sell portfolio securities to meet daily margin requirements
at a time when it may be disadvantageous to do so. In addition, the Fund may be
required to make delivery of the instruments underlying futures contracts it
holds. The inability to close options and futures positions also could have an
adverse impact on the ability to effectively hedge the Fund.
    

   The Fund will minimize the risk that it will be unable to close out a 
futures contract by only entering into futures which are traded on national 
futures exchanges and for which there appears to be a liquid secondary 
market. The principal interest rate futures exchanges in the United States 
are the Board of Trade of the City of Chicago and the Chicago Mercantile 
Exchange. 

   The risk of loss in trading futures contracts in some strategies can be 
substantial, due both to the low margin deposits required, and the extremely 
high degree of leverage involved in futures pricing. As a result, a 
relatively small price movement in a futures contract may result in immediate 
and substantial loss (as well as gain) to the investor. For example, if at 
the time of purchase, 10% of the value of the futures contract is deposited 
as margin, a subsequent 10% decrease in the value of the futures contract 
would result in a total loss of the margin deposit, before any deduction for 
the transaction costs, if the account were then closed out. A 15% decrease 
would result in a loss equal to 150% of the original margin deposit if the 
contract were closed out. Thus, a purchase or sale of a futures contract may 
result in losses in excess of the amount invested in the contract. However, 
because the futures strategies of the Fund are engaged in only for hedging 
purposes, the Adviser does not believe that the Fund is subject to the risks 
of loss frequently associated with futures transactions. The Fund would 
presumably have sustained comparable losses if, instead of the futures 
contract, it had invested in the underlying financial instrument and sold it 
after the decline. 

   Utilization of futures transactions by the Fund does involve the risk of 
imperfect or no correlation where the securities underlying futures contracts 
have different maturities or other characteristics than the portfolio 
securities being hedged. It is also possible that the Fund could both lose 
money on futures contracts and also experience a decline in value of its 
portfolio securities. There is also the risk of loss by the Fund of margin 
deposits in the event of bankruptcy of a broker with whom the Fund has an 
open position in a futures contract or related option. 

   Most futures exchanges limit the amount of fluctuation permitted in 
futures contract prices during a single trading day. The daily limit 
establishes the maximum amount that the price of a futures contract may vary 
either up or down from the previous day's settlement price at the end of a 
trading session. Once the daily limit has been reached in a particular type 
of contract, no trades may be made on that day at a price beyond that limit. 
The daily limit governs only price movement during a particular trading day 
and therefore does not limit potential losses, because the limit may prevent 
the liquidation of unfavorable positions. Futures contract prices have 
occasionally moved to the daily limit for several consecutive trading days 
with little or no trading, thereby preventing prompt liquidation of future 
positions and subjecting some futures traders to substantial losses. 

   Federal Tax Treatment of Futures Contracts  The Fund is required for 
federal income tax purposes to recognize as income for each taxable year its 
net unrealized gains and losses on certain futures contracts held as of the 
end of the year as well as those actually realized during the year. In most 
cases, any gain or loss recognized with respect to a futures contract is 
considered to be 60% long-term capital gain or loss and 40% short-term 
capital gain or loss, without regard to the holding period of the contract. 
Furthermore, sales of futures contracts which are intended to hedge against a 
change in the value of securities held by the Fund may affect the holding 
period of such securities and, consequently, the nature of the gain or loss 
on such securities upon disposition. The Fund may be required to defer the 
recognition of losses on futures contracts to the extent of any unrecognized 
gains on related positions held by the Fund. 

   In order for the Fund to continue to qualify for federal income tax treatment
as a regulated investment company, at least 90% of its gross income for a
taxable year must be derived from qualifying income; i.e., dividends, interest,
income derived from loans of securities, gains from the sale of securities or of
foreign currencies or other income derived with respect to the Fund's business
of investing in securities. In addition, gains realized on the sale or other


                                                                             B-5

<PAGE>
disposition of securities held for less than three months must be limited to
less than 30% of the Fund's annual gross income. It is anticipated that any net
gain realized from the closing out of futures contracts will be considered gain
from the sale of securities and therefore be qualifying income for purposes of
the 90% requirement. In order to avoid realizing excessive gains on securities
held less than three months, the Fund may be required to defer the closing out
of futures contracts beyond the time when it would otherwise be advantageous to
do so. It is anticipated that unrealized gains on futures contracts, which have
been open for less than three months as of the end of the Fund's fiscal year and
which are recognized for tax purposes, will not be considered gains on sales of
securities held less than three months for the purpose of the 30% test.

   The Fund will distribute to shareholders annually any net capital gains 
which have been recognized for federal income tax purposes (including 
unrealized gains at the end of the Fund's fiscal year) on futures 
transactions. Such distributions will be combined with distributions of 
capital gains realized on the Fund's other investments and shareholders will 
be advised on the nature of the transactions. 


   
                                 RISK FACTORS 
    

   The Fund invests primarily in the obligations of New York state 
government, state agencies, state authorities and various local governments, 
including counties, cities, towns, special districts, and authorities. In 
general, the credit quality and credit risk of any issuer's debt depend on 
the state and local economy, the health of the issuer's finances, the amount 
of the issuer's debt, the quality of management, and the strength of legal 
provisions in debt documents that protect debt holders. Credit risk is 
usually lower wherever the economy is strong, growing and diversified; 
financial operations are sound; and the debt burden is reasonable. 

   The average rating among American states for full faith and credit state 
debt is "double-A" by Moody's Investors Service and Standard & Poor's 
Corporation. Against this measure and the criteria listed above, the credit 
risk associated with direct obligations of the State of New York and State 
agencies and authorities, including general obligation and revenue bonds, 
"moral obligation" bonds, lease debt, and notes, compares somewhat 
unfavorably. During most of the last two decades, the State's general 
obligation bonds have been rated just below this average by both rating 
agencies. Additionally, the State's credit quality could be characterized as 
more volatile than that of other states, since the State's credit rating has 
been upgraded and downgraded much more often than usual. This rating has 
fluctuated between "double-A" and "single-A" since the early 1970s. 
Nonetheless, during this period the State's obligations could still be 
characterized as providing upper medium grade security, with a strong 
capacity for timely repayment of debt. 

   
   The wealth of New York State, as well as the size and diversity of its 
economy, serve to limit the credit risk of its securities. New York ranks 
third among the states in per capita personal income, which is 19% above the 
U.S. average. During most of the 1980s, economic indicators for New York, 
including income and employment growth and unemployment rates, outperformed 
the nation as a whole. The engine of growth for the State in the past decade 
was the surge in financial and other services, especially in New York City. 
Manufacturing centers in Upstate New York, which more closely parallel the 
midwestern economy, suffered during the 1970s and early 1980s. The upstate 
economy continues to benefit from the free trade treaty with Canada and the 
strength of U.S. exports in general. 

   Credit risk in New York State is heightened by a large and increasing debt 
burden, frequently marginal financial operations, limited revenue-raising 
flexibility, and the uncertainty of the future credit quality of New York 
City, which comprises 40% of the State's population and economy. Combined 
State and local debt per capita is about 50% above the U.S. average, and debt 
service expenditures have been growing as a claim on the State budget. New 
York's debt structure is also complicated. To circumvent voter approval, most 
State debt is issued by agencies, is not backed by the State's full faith and 
credit and therefore has lower credit ratings. In the past, the State had to 
rely on short-term borrowing to meet its obligations, but this practice has 
ended. 
    



B-6
<PAGE>

   
   Buoyed by rapid economic growth in the mid-1980s, the State's financial 
operations generated surpluses. Beginning in 1988, however, unforeseen 
consequences of federal tax reform, combined with a weakening economy, 
resulted in a series of state budget deficits. New York's heavy commitment to 
local aid and social welfare programs allowed expenditure growth to exceed 
available revenues. This lack of budgetary discipline caused the State's 
credit ratings to fall. Moreover, New York's ability to raise revenues is 
limited, since combined State and local taxes are among the highest in the 
nation as a percent of personal income. Recent state budgets have been 
balanced, and the prospects for reform of debt management are improving. 
Recent political events pose uncertainty for the State. Governor George 
Pataki is committed to reducing taxation. Unless expenditures also are cut, 
the State will once again experience fiscal stress. 
    

   New York State's future credit quality will be heavily influenced by the 
future of New York City. As the City's economic boom in the 1980s lifted the 
State, the severe downturn in the financial services and real estate sectors, 
which are concentrated in the City, has been serving as a drag on the State 
economy. Stabilization or recovery in these areas is crucial to the economic 
and fiscal health of the City and the State. Moreover, the City faces 
daunting challenges in combatting deteriorating infrastructure and serious 
social problems of housing, health, education and public safety. So far, City 
government has demonstrated an ability to keep abreast of these problems, but 
the City's and the State's ability to meet these challenges will be a 
continuing risk factor. 


                            YIELD AND TOTAL RETURN 

   
   The yield of the Fund for the 30-day period ended November 30, 1995 was 
+4.97%. 

   The average annual total return of the Fund for the one- and five-year 
periods ending November 30, 1995 was +19.90% and +9.13%, respectively. The 
average annual total return for the Fund since its inception on April 7, 1986 
is +7.65%. 
    


                             PERFORMANCE MEASURES 

   
   Vanguard may use reprinted material discussing The Vanguard Group, Inc. or 
any of the member funds of the Vanguard Group of Investment Companies. 
    

   Vanguard New York Insured Tax-Free Fund may use one or more, either 
singularly or in a composite, of the following unmanaged indexes for 
comparative performance purposes: 

Standard & Poor's 500 Composite Stock Price Index--is a well-diversified list 
of 500 companies representing the U.S. Stock Market. 

Wilshire 5000 Equity Index--consists of more than 6,000 common equity 
securities, covering all stocks in the U.S. for which daily pricing is 
available. 

Wilshire 4500 Equity Index--consists of all stocks in the Wilshire 5000 
except for the 500 stocks in the Standard and Poor's 500 Index. 

Russell 3000 Stock Index--a diversified portfolio of approximately 3,000 
common stocks accounting for over 90% of the market value of publicly traded 
stocks in the U.S. 

Russell 2000 Stock Index--a subset of approximately 2,000 of the smallest 
stocks contained in the Russell 3000; a widely-used benchmark for small 
capitalization common stocks. 

Morgan Stanley Capital International EAFE Index--is an arithmetic, market 
value-weighted average of the performance of over 900 securities listed on 
the stock exchanges of countries in Europe, Australia and the Far East. 

   
Goldman Sachs 100 Convertible Bond Index--currently includes 71 bonds and 29 
preferreds. The original list of names was generated by screening for 
convertible issues of $100 million or greater in market capitalization. The 
index is priced monthly. 
    

Salomon Brothers GNMA Index--includes pools of mortgages originated by 
private lenders and guaranteed by the mortgage pools of the Government 
National Mortgage Association. 

                                                                             B-7
<PAGE>


   
Salomon Brothers High-Grade Corporate Bond Index--consists of publicly 
issued, non-convertible corporate bonds rated Aa or Aaa. It is a 
value-weighted, total return index, including approximately 800 issues with 
maturities of 12 years or greater. 
    

Lehman Long-Term Treasury Bond--is composed of all bonds covered by the 
Shearson Lehman Hutton Treasury Bond Index with maturities of 10 years or 
greater. 

Merrill Lynch Corporate & Government Bond--consists of over 4,500 U.S. 
Treasury, Agency and investment grade corporate bonds. 

Lehman Corporate (Baa) Bond Index--all publicly offered fixed-rate 
nonconvertible domestic corporate bonds rated Baa by Moody's, with a maturity 
longer than 1 year and with more than $25 million outstanding. This index 
includes over 1,000 issues. 

   
Lehman Brothers Long-Term Corporate Bond Index--is a subset of the Lehman 
Corporate Bond Index covering all corporate, publicly issued, fixed-rate, 
nonconvertible U.S. debt issues rated at least Baa, with at least $50 million 
principal outstanding and maturity greater than 10 years. 
    

Bond Buyer Municipal Index (20 Year) Bond--is a yield index on current coupon 
high-grade general obligation municipal bonds. 

Standard & Poor's Preferred Index--is a yield index based upon the average 
yield of four high- grade, non-callable preferred stock issues. 

NASDAQ Industrial Index--is composed of more than 3,000 industrial issues. It 
is a value-weighted index calculated on price change only and does not 
include income. 

Composite Index--70% Standard & Poor's 500 Index and 30% NASDAQ Industrial 
Index. 

   
Composite Index--35% Standard & Poor's 500 Index and 65% Lehman Brothers 
Long-Term Corporate Bond Index. 
    

Composite Index--65% Standard & Poor's 500 Index and 35% Salomon Brothers 
High-Grade Bond Index. 

   
Lehman Brothers Aggregate Bond Index--is a market-weighted index that 
contains individually priced U.S. Treasury, agency, corporate, and mortgage 
pass-through securities corporate rated BBB- or better. The Index has a 
market value of over $4 trillion. 

Lehman Brothers Mutual Fund Short (1-5) Government/Corporate Index--is a 
market-weighted index that contains individually priced U.S. Treasury, 
agency, and corporate investment grade bonds rated BBB- or better with 
maturities between 1 and 5 years. The index has a market value of over $1.3 
trillion. 

Lehman Brothers Mutual Fund Intermediate (5-10) Government/Corporate 
Index--is a market- weighted index that contains individually priced U.S. 
Treasury, agency, and corporate securities rated BBB- or better with 
maturities between 5 and 10 years. The index has a market value of over $600 
billion. 

Lehman Brothers Mutual Fund Long (10+) Government/Corporate Index--is a 
market-weighted index that contains individually priced U.S. Treasury, 
agency, and corporate securities rated BBB- or better with maturities greater 
than 10 years. The index has a market value of over $900 billion. 
    

Lipper Small Company Growth Fund Average--the average performance of small 
company growth funds as defined by Lipper Analytical Services, Inc. Lipper 
defines a small company growth fund as a fund that by prospectus or portfolio 
practice, limits its investments to companies on the basis of the size of the 
company. From time to time, Vanguard may advertise using the average 
performance and/or the average expense ratio of the small company growth 
funds. (This fund category was first established in 1982. For years prior to 
1982, the results of the Lipper Small Company Growth category were estimated 
using the returns of the Funds that constituted the Group at its inception.) 

B-8

<PAGE>



   
Lipper General Equity Fund Average--an industry benchmark of average general 
equity funds with similar investment objectives and policies, as measured by 
Lipper Analytical Services, Inc. 

Lipper Fixed Income Fund Average--an industry benchmark of average fixed 
income funds with similar investment objectives and policies, as measured by 
Lipper Analytical Services, Inc. 

Lipper Balanced Fund Average--an industry benchmark of average balanced funds 
with similar investment objectives and policies, as measured by Lipper 
Analytical Services, Inc. 

Lipper Non-Government Money Market Fund Average--an industry benchmark of 
average non- government money market funds with similar investment objectives 
and policies, as measured by Lipper Analytical Services, Inc. 

Lipper Government Money Market Fund Average--an industry benchmark of average 
government money market funds with similar investment objectives and 
policies, as measured by Lipper Analytical Services, Inc. 
    


                            INVESTMENT MANAGEMENT 

   The Fund receives all investment advisory services on an "internalized," 
at-cost basis from an experienced investment management staff employed 
directly by The Vanguard Group, Inc. ("Vanguard"), a subsidiary jointly owned 
by the Fund and the other Funds in The Vanguard Group of Investment 
Companies. The investment management staff is supervised by the senior 
officers of the Fund. 

   The investment management staff is responsible for: maintaining the 
specified standards; making changes in specific issues in light of changes in 
the fundamental basis for purchasing such securities; and adjusting the Fund 
to meet cash inflow (or outflow), which reflects net purchases and exchanges 
of shares by investors (or net redemptions of shares) and reinvestment of the 
Fund's income. 

   
   A change in securities held by the Fund is known as "portfolio turnover" 
and may involve the payment of the Fund of dealer mark-ups, underwriting 
commissions and other transaction costs on the sales of securities as well as 
on the reinvestment of the proceeds in other securities. The annual portfolio 
turnover rate for the Fund is set forth under the heading "Financial 
Highlights" in the Fund's Prospectus. The portfolio turnover rate is not a 
limiting factor when management deems it desirable to sell or purchase 
securities. It is impossible to predict whether or not the portfolio turnover 
rate in future years will vary significantly from the rates in recent years. 
    


                              PURCHASE OF SHARES 

   
   The Fund reserves the right in its sole discretion (i) to suspend the 
offering of its shares, (ii) to reject purchase orders when in the judgment 
of management such rejection is in the best interest of the Fund, and (iii) 
to reduce or waive the minimum investment for or any other restriction on 
initial and subsequent investments under circumstances where certain 
economies can be achieved in sales of the Fund's shares. 
    

   Stock Certificates  Your purchase will be made in full and fractional 
shares of the Fund calculated to three decimal places. Shares are normally 
held on deposit for shareholders by the Fund, which will send to shareholders 
a statement of shares owned at the time of each transaction. This saves the 
shareholders the trouble of safekeeping the certificates and saves the Fund 
the cost of issuing certificates. Share certificates are, of course, 
available at any time upon written request at no additional cost to 
shareholders. No certificates will be issued for fractional shares. 


                             REDEMPTION OF SHARES 

   The Fund may suspend redemption privileges or postpone the date of payment
(i) during any period that the New York Stock Exchange is closed, or trading on
the Exchange is restricted as determined by the Securities and Exchange
Commission (the "Commission"), (ii) during any period when an emergency exists

                                                                             B-9
<PAGE>

as defined by the rules of the Commission as a result of which it is not
reasonably practicable for the Fund to dispose of securities owned by it, or
fairly to determine the value of its assets, and (iii) for such other periods as
the Commission may permit.

   If the Board of Trustees determines that it would be detrimental to the 
best interests of the remaining shareholders of the Fund to make payment 
wholly or partly in cash, the Fund may pay the redemption price in whole or 
in part by a distribution in kind of securities held by the Fund in lieu of 
cash in conformity with applicable rules of the Commission. Investors may 
incur brokerage charges on the sale of such securities so received in payment 
of redemptions. 

   No charge is made by the Fund for redemptions except for wire redemptions 
of under $5,000 which may be charged a maximum fee of $5.00. Any redemption 
may be more or less than the shareholder's cost depending on the market value 
of the securities held by the Fund. 

   
   Signature Guarantees  To protect your account, the Fund and Vanguard from 
fraud, signature guarantees are required for certain redemptions. Signature 
guarantees enable the Fund to verify the identity of the person who has 
authorized a redemption from your account. Signature guarantees are required 
in connection with: (1) all redemptions, regardless of the amount involved, 
when the proceeds are to be paid to someone other than the registered owners; 
and (2) share transfer requests. 
    

   A guarantor must be a bank, a trust company, a member firm of a domestic 
stock exchange, a foreign branch of any of the foregoing or any other 
guarantor that Vanguard deems to be acceptable. Notaries public are not 
acceptable guarantors. 

   
   The signature guarantees must appear either: (1) on the written request 
for redemption or transfer, (2) on a separate instrument for assignment 
("stock power") which should specify the total number of shares to be 
redeemed, or (3) on all stock certificates tendered for redemption and, if 
shares held by the Fund are also being redeemed, on the letter or stock 
power. 
    
 


B-10
<PAGE>
                            MANAGEMENT OF THE FUND 

OFFICERS AND TRUSTEES 

   
   The Fund's Officers, under the supervision of the Board of Trustees, 
manage the day-to-day operations of the Fund. The Trustees, set broad 
policies for the Fund and choose its Officers. 
    

   A list of the Trustees and Officers of the Fund and a brief statement of 
their present positions and principal occupations during the past 5 years is 
set forth below. 

   The mailing address of the Fund's Trustees and Officers is Post Office Box 
876, Valley Forge, PA 19482. 

   
JOHN C. BOGLE, Chairman and Trustee* 
 Chairman and Director of The Vanguard Group, Inc., and of each of the 
 investment companies in The Vanguard Group; Director of The Mead Corporation 
 and General Accident Insurance. 

JOHN J. BRENNAN, President, Chief Executive Officer & Trustee* 
 President, Chief Executive Officer and Director of the Fund, The Vanguard 
 Group, Inc. and of each of the investment companies in The Vanguard Group. 

ROBERT E. CAWTHORN, Trustee 
 Chairman of Rhone-Poulenc Rorer, Inc.; Direc- tor of Sun Company, Inc.. 

BARBARA BARNES HAUPTFUHRER, Trustee 
 Director of The Great Atlantic and Pacific Tea Company, Alco Standard Corp., 
 Raytheon Company, Knight-Ridder, Inc., and Massachusetts Mutual Life 
 Insurance Co. and Trustee Emerita of Wellesley College. 

BURTON G. MALKIEL, Trustee 
 Chemical Bank Chairman's Professor of Economics, Princeton University; 
 Director of Prudential Insurance Co. of America, Amdahl Corporation, Baker 
 Fentress & Co., The Jeffrey Co., and Southern New England Communications 
 Company. 

ALFRED M. RANKIN, JR., Trustee 
 Chairman, President, and Chief Executive Officer of NACCO Industries, Inc.; 
 Director of The BFGoodrich Company and The Standard Products Company. 

JOHN C. SAWHILL, Trustee 
 President and Chief Executive Officer, The Nature Conservancy; formerly, 
 Director and Senior Partner, McKinsey & Co.; President, New York University; 
 Director of Pacific Gas and Electric Company and NACCO Industries. 

JAMES O. WELCH, Jr., Trustee 
 Retired Chairman of Nabisco Brands Inc., retired Vice Chairman and Director 
 of RJR Nabisco; Director of TECO Energy, Inc. and Director of Kmart 
 Corporation. 

J. LAWRENCE WILSON, Trustee 
 Chairman and Chief Executive Officer of Rohm & Haas Company; Director of 
 Cummins Engine Company and Trustee of Vanderbilt University. 

RAYMOND J. KLAPINSKY, Secretary* 
 Senior Vice President and Secretary of The Vanguard Group, Inc.; Secretary 
 of each of the investment companies in The Vanguard Group. 

RICHARD F. HYLAND, Treasurer* 
 Treasurer of The Vanguard Group, Inc. and of each of the investment 
 companies in The Vanguard Group. 

KAREN E. WEST, Controller* 
 Principal of The Vanguard Group, Inc.; Controller of each of the investment 
 companies in The Vanguard Group. 

- ------ 
* Officers of the Fund are "interested persons" as defined in the Investment 
  Company Act of 1940. 
    

THE VANGUARD GROUP 

   Vanguard New York Insured Tax-Free Fund is a member of The Vanguard Group 
of Investment Companies. Through their jointly-owned subsidiary, The Vanguard 
Group, Inc. ("Vanguard"), the Fund and the other Funds in the Group obtain 
at-cost virtually all of their corporate management, administrative and 
distribution services. Vanguard also provides investment advisory services on 
an at-cost basis to certain Vanguard Funds, including the Vanguard New York 
Insured Tax-Free Fund. 

                                                                            B-11

<PAGE>

   Vanguard employs a supporting staff of management and administrative 
personnel needed to provide the requisite services to the Funds and also 
furnishes the Funds with necessary office space, furnishings and equipment. 
Each Fund pays its share of Vanguard's net expenses which are allocated among 
the Funds under methods approved by the Board of Trustees (Directors) of each 
Fund. In addition, each Fund bears its own direct expenses such as legal, 
auditing and custodian fees. 

   
    The Fund's Officers are also officers and employees of Vanguard. No officer 
or employee owns, or is permitted to own, any securities of any external 
adviser for the Funds. 
    
   The Vanguard Group adheres to a Code of Ethics established pursuant to Rule
17j-1 under the Investment Company Act of 1940. The Code is designed to prevent
unlawful practices in connection with the purchase or sale of securities by
persons associated with Vanguard. Under Vanguard's Code of Ethics, certain
officers and employees of Vanguard who are considered access persons are
permitted to engage in personal securities transactions. However, such
transactions are subject to procedures and guidelines substantially similar to
those recommended by the mutual fund industry and approved by the U.S.
Securities and Exchange Commission.
    
   The Vanguard Group was established and operates under a Funds' Service
Agreement which was approved by the shareholders of each of the Funds. The
Funds' Service Agreement provides for the following arrangement: (1) each
Vanguard Fund may invest a maximum of 0.40% of its net assets in Vanguard; and
(2) there is no restriction on the maximum aggregate cash investment that the
Vanguard Funds may make in Vanguard. The amounts which each of the Funds has
invested are adjusted from time to time in order to maintain the proportionate
relationship between each Fund's relative net assets and its contribution to
Vanguard's capital. At November 30, 1995, Vanguard New York Insured Tax-Free
Fund had contributed capital of $102,000 to Vanguard representing .5% of
Vanguard's capitalization.
    
   Management  Corporate management and administrative services include: (1)
executive staff; (2) accounting and financial; (3) legal and regulatory; (4)
shareholder account maintenance; (5) monitoring and control of custodian
relationships; (6) shareholder reporting; and (7) review and evaluation of
advisory and other services provided to the Funds by third parties. During the
fiscal year ended November 30, 1995, the Funds share of Vanguard's actual net
costs of operations relating to management and administrative services
(including transfer agency) totaled approximately $1,343,000.
    
   Distribution  Vanguard provides all distribution and marketing activities for
the Funds in the Group. Vanguard Marketing Corporation, a wholly-owned
subsidiary of The Vanguard Group, Inc., acts as Sales Agent for shares of the
Funds in connection with any sales made directly to investors in the states of
Florida, Missouri, New York, Ohio, Texas and such other states as it may be
required.
    
   The principal distribution expenses are for advertising, promotional
materials and marketing personnel. Distribution services may also include
organizing and offering to the public, from time to time, one or more new
investment companies which will become members of the Group. The Trustees
(Directors) and officers of Vanguard determine the amount to be spent annually
on distribution activities, the manner and amount to be spent on each Fund, and
whether to organize new investment companies.
    
   One half of the distribution expenses of a marketing and promotional nature
is allocated among the Funds based upon their relative net assets. The remaining
one half of these expenses is allocated among the Funds based upon each Fund's
sales for the preceding 24 months relative to the total sales of the Funds as a
Group, provided, however, that no Fund's aggregate quarterly rate of
contribution for distribution expenses of a marketing and promotional nature
shall exceed 125% of the average distribution expense rate for the Group, and
that no Fund shall incur annual distribution expenses in excess of 20/100 of 1%
of its average month-end net assets. During the year ended November 30, 1995,
the Fund paid approximately $169,000 of the Group's distribution and marketing
expenses.

    
   Investment Advisory Services  Vanguard also provides investment advisory
services to the Fund, Vanguard Municipal Bond Fund, Vanguard Money Market
Reserves, Vanguard California Tax- Free Fund, Vanguard Pennsylvania Tax-Free
Fund, Vanguard New Jersey Tax-Free Fund, Vanguard Florida Insured Tax-Free Fund,
Vanguard Ohio Tax-Free Fund, Vanguard Admiral Funds, Vanguard International
Equity Index Fund, Vanguard Balanced Index Fund, Vanguard Institutional Index
Fund, Vanguard Index Trust, Vanguard Tax-Managed Fund, the Aggressive Growth
Portfolio of Vanguard Horizon Fund, Vanguard Bond Index Fund, several Portfolios
    
B-12
<PAGE>

   
of Vanguard Variable Insurance Fund, several Portfolios of Vanguard Fixed Income
Securities Fund, a portion of Vanguard/Windsor II, a portion of Vanguard/Morgan
Growth Fund as well as several indexed separate accounts. These services are
provided on an at-cost basis from a money management staff employed directly by
Vanguard. The compensation and other expenses of this staff are paid by the
Funds utilizing these services. During the years ended November 30, 1993, 1994
and 1995 the Fund paid approximately $65,000, $89,000 and $101,000 of Vanguard's
investment advisory expenses.

   Remuneration of Trustees and Officers  The Fund pays each Trustee, who is 
not also an Officer, an annual fee plus travel and other expenses incurred in 
attending Board meetings. During the year ended November 30, 1995, the Fund 
paid $3,000 in Trustees' expenses. The Fund's Officers and employees are paid 
by Vanguard which, in turn, is reimbursed by the Fund, and each other Fund in 
the Group, for its proportionate share of Officers' and employees' salaries 
and retirement benefits. During the year ended November 30, 1995, the Fund's 
proportionate share of remuneration paid to all Officers of the Fund as a 
group was approximately $   o    . 

   Upon retirement, Trustees who are not Officers are paid an annual fee 
based upon the number of years of service on the Board. The fee is equal to 
$1,000 for each year of service up to a maximum of $15,000. Under its 
Retirement Plan, Vanguard contributes annually an amount equal to 10% of each 
Officer's annual compensation plus 5.7% of that part of the Officer's 
compensation during the year, if any, that exceeds the Social Security 
Taxable Wage Base then in effect. Under Vanguard's Thrift Plan, all employees 
are permitted to make pre-tax contributions in a maximum amount equal to 4% 
of total compensation. Vanguard matches the basic contribution on a 100% 
basis. During the year ended November 30, 1995 the Fund's proportionate share 
of retirement benefits paid to all Officers of the Fund, as a group, was 
approximately $   o    . 
    
<PAGE>


   
   The following table provides detailed information with respect to the 
amounts paid or accrued for the Trustees for the fiscal year ended November 
30, 1995. 


                   VANGUARD NEW YORK INSURED TAX-FREE FUND 
                              COMPENSATION TABLE 

<TABLE>
<CAPTION>


                                                                                         Total 
                                                  Pension or                         Compensation 
                                                  Retirement         Estimated         From All 
                                Aggregate      Benefits Accrued        Annual          Vanguard 
                               Compensation       As Part of       Benefits Upon      Funds Paid 
     Names of Trustees          From Fund       Fund Expenses        Retirement     to Trustees(3) 
     -----------------       --------------   ----------------    ---------------   -------------- 
<S>                                <C>               <C>              <C>               <C>     
John C. Bogle(1)(2)  ......         --                --                 --               -- 
John J. Brennan(2)  .......         --                --                 --               -- 
Barbara Barnes Hauptfuhrer         $342              $60              $15,000           $60,000 
Robert E. Cawthorn  .......        $342              $50              $13,000           $60,000 
Burton G. Malkiel  ........        $342              $40              $15,000           $60,000 
Alfred M. Rankin, Jr.  ....        $342              $31              $15,000           $60,000 
John C. Sawhill  ..........        $342              $37              $15,000           $60,000 
James O. Welch, Jr.  ......        $342              $46              $15,000           $60,000 
J. Lawrence Wilson  .......        $342              $33              $15,000           $60,000
</TABLE>


- ------ 
(1) For the period reported in this table, Mr. Bogle was the Fund's Chief 
    Executive Officer, and therefore an "Interested Trustee." 
(2) As "Interested Trustees," Messrs. Bogle and Brennan receive no 
    compensation for their service as Trustees. 
(3) The amounts reported in this column reflect the total compensation paid 
    to each Trustee for their service as Director or Trustee of 33 Vanguard 
    Funds. 
    


                   DESCRIPTION OF SHARES AND VOTING RIGHTS 

   The Fund was organized as a Pennsylvania Trust on October 16, 1985. 

   The Declaration of Trust, as amended and restated on January 15, 1986, 
permits the Trustees to issue an unlimited number of shares of beneficial 
interest, without par value, from an unlimited number of separate classes 
("Portfolios") of shares. Currently, the Fund is offering shares of one 
Portfolio. 

   The shares of the Fund are fully paid and nonassessable, except as set 
forth under "Shareholder and Trustee Liability," and have no preference as to 
conversion, exchange, dividends, retirement or other features. The shares of 
the Fund have no pre-emptive rights. The shares of the Fund have non- 
cumulative voting rights, which means that the holders of more than 50% of 
the shares voting for the election of Trustees can elect 100% of the Trustees 
if they choose to do so. A shareholder is entitled to one vote for each full 
share held (and a fractional vote for each fractional share held), then 
standing in his name on the books of the Fund. On any matter submitted to a 
vote of shareholders, all shares of the Fund then issued and outstanding and 
entitled to vote, irrespective of the class, shall be voted in the aggregate 
and not by class: except (i) when required by the Investment Company Act of 
1940, shares shall be voted by individual class; and (ii) when the matter 
does not affect any interest of a particular class, then only shareholders of 
the affected class or classes shall be entitled to vote thereon. 

   The Fund will continue without limitation of time, provided, however that: 

       1) Subject to the majority vote of the holders of shares of the Fund 
   outstanding, the Trustees may sell or convert the assets of the Fund to 
   another investment company in exchange for shares of such investment 
   company, and distribute such shares, ratably among the shareholders of the 
   Fund.
 
       2) Subject to the majority vote of shares of the Fund outstanding, the 
   Trustees may sell and convert into money the assets of the Fund and 
   distribute such assets ratably among the shareholders of the Fund; and 


B-14


<PAGE>


   Upon completion of the distribution of the remaining proceeds or the 
remaining assets of any Portfolio as provided in paragraphs 1) and 2) above 
the Fund shall terminate and the Trustees shall be discharged of any and all 
further liabilities and duties hereunder and the right, title and interest of 
all parties shall be cancelled and discharged. 

   Shareholder and Trustee Liability  Under Pennsylvania law, shareholders of 
such a Trust may under certain circumstances, be held personally liable as 
partners for the obligations of the Fund. Therefore, the Declaration of Trust 
contains an express disclaimer of shareholder liability for acts or 
obligations of the Fund and requires that notice of such disclaimer be given 
in each agreement, obligation, or instrument entered into or executed by the 
Fund or the Trustees. The Declaration of Trust provides for indemnification 
out of the Fund property of any shareholder held personally liable for the 
obligations of the Fund. The Declaration of Trust also provides that the Fund 
shall, upon request, assume the defense of any claim made against any 
shareholder for any act or obligation of the Fund and satisfy any judgment 
thereon. Thus, the risk of a shareholder incurring financial loss on account 
of shareholder liability is limited to circumstances in which the Fund itself 
would be unable to meet its obligations. 

   
   The Declaration of Trust further provides that the Trustees will not be 
liable for errors of judgment or mistakes of fact or law, but nothing in the 
Declaration of Trust protects a Trustee against any liability to which he 
would otherwise be subject by reason of willful misfeasance, bad faith, gross 
negligence, or reckless disregard of the duties involved in the conduct of 
his office. 
    

                             FINANCIAL STATEMENTS 

   
   The Fund's financial statements for the year ended November 30, 1995, 
including the financial highlights for each of the five fiscal years in the 
period ended November 30, 1995, appearing in the Vanguard New York Insured 
Tax-Free Fund's 1995 Annual Report to Shareholders, and the report thereon of 
Price Waterhouse LLP, independent accountants, also appearing therein, are 
incorporated by reference in this Statement of Additional Information. The 
Fund's 1995 Annual Report to Shareholders is enclosed with this Statement of 
Additional Information. 
    


                                                                            B-15

<PAGE>

         APPENDIX A--DESCRIPTION OF MUNICIPAL BONDS AND THEIR RATINGS 

   
   Municipal Bonds--General  Municipal Bonds generally include debt 
obligations issued by states and their political subdivisions, and duly 
constituted authorities, not-for-profit corporations, and corporations, to 
obtain funds to construct, repair or improve various public facilities such 
as airports, bridges, highways, hospitals, housing, schools, streets and 
water and sewer works. Municipal Bonds may also be issued to refinance 
outstanding obligations as well as to obtain funds for general operating 
expenses and for loan to other public institutions and facilities. 
    

   The two principal classifications of Municipal Bonds are "general 
obligation" and "revenue" or "special tax" bonds. General obligation bonds 
are secured by the issuer's pledge of its full faith, credit and taxing power 
for the payment of principal and interest. Revenue or special tax bonds are 
payable only from the revenues derived from a particular facility or class of 
facilities or, in some cases, from the proceeds of a special excise or other 
tax, but not from general tax revenues. The Fund may also invest in 
tax-exempt industrial development bonds, short-term municipal obligations 
(rated SP-1+ of SP-1 by Standard & Poor's Corp. or MIG by Moody's Investors 
Service), project notes, demand notes and tax- exempt commercial papers 
(rated A-1 by Standard & Poor's Corp. or P-1 by Moody's Investors Service). 

   Industrial revenue bonds in most cases are revenue bonds and generally do 
not have the pledge of the credit of the Issuer. The payment of the principal 
and interest on such industrial revenue bonds is dependent solely on the 
ability of the user of the facilities financed by the bonds to meet its 
financial obligations and the pledge, if any, of real and personal property 
so financed as security for such payment. 

   Short-term municipal obligations issued by states, cities, municipalities 
or municipal agencies, include Tax Anticipation Notes, Revenue Anticipation 
Notes, Bond Anticipation Notes, Construction Loan Notes and Short-Term 
Discount Notes. 

   Project Notes are instruments issued by the Department of Housing and 
Urban Development but issued by a state or local housing agency. While the 
issuing agency has the primary obligation on such Project notes, they are 
also secured by the full faith and credit of the United States. 

   
   Note obligations with demand or put options may have a stated maturity in 
excess of one year, but permit any holder to demand payment of principal plus 
accrued interest upon a specified number of days' notice. Frequently, such 
obligations are secured by letters of credit or other credit support 
arrangements provided by banks. The issuer of such notes normally has a 
corresponding right, after a given period, to repay in its discretion, the 
outstanding principal of the note plus accrued interest upon a specific 
number of days' notice to the bondholders. The interest rate on a demand note 
may be based upon a known lending rate, such as a bank's prime rate, and be 
adjusted when such rate changes, or the interest rate on a demand note may be 
a market rate that is adjusted at specified intervals. The demand notes in 
which the Fund will invest are payable on not more than one year's notice. 
Each note purchased by the Fund will meet the quality criteria set out above 
for the Fund. 
    

   The yields of Municipal Bonds depend on, among other things, general money 
market conditions, conditions in the Municipal Bond market, the size of a 
particular offering, the maturity of the obligation, and the rating of the 
issue. The ratings of Moody's Investors Service, Inc. and Standard & Poor's 
Corporation represent their opinions of the quality of the Municipal Bonds 
rated by them. It should be emphasized that such ratings are general and are 
not absolute standards of quality. Consequently, Municipal Bonds with the 
same maturity, coupon and rating may have different yields, while Municipal 
Bonds of the same maturity and coupon, but with different ratings may have 
the same yield. It will be the responsibility of the investment management 
staff to appraise independently the fundamental quality of the bonds held by 
the Fund. 

   Municipal Bonds are sometimes purchased on a "when-issued" basis meaning 
the Fund has committed to purchasing certain specified securities at an 
agreed upon price when they are issued. The period between commitment date 
and issuance date can be a month or more. It is possible that the securities 
will never be issued and the commitment canceled. 

   From time to time proposals have been introduced before Congress to restrict
or eliminate the Federal income tax exemption for interest on Municipal Bonds.
Similar proposals may be introduced in the future. If any such proposal were


B-16

<PAGE>

enacted, it might restrict or eliminate the ability of the Fund to achieve its
investment objective. In that event, the Fund's Trustees and officers would
reevaluate its investment objective and policies and consider recommending to
its shareholders changes in such objective and policies.

   Similarly, from time to time proposals have been introduced before State 
and local legislatures to restrict or eliminate the State and local income 
tax exemption for interest on Municipal Bonds. Similar proposals may be 
introduced in the future. If any such proposal were enacted, it might 
restrict or eliminate the ability of each Portfolio to achieve its respective 
investment objective. In that event, the fund's trustees and officers would 
reevaluate its investment objective and policies and consider recommending to 
its shareholders changes in such objective and policies. (For more 
information please refer to "Risk Factors" on page 5.) 

   Ratings. Excerpts from Moody's Investors Service, Inc.'s Municipal Bond 
ratings: Aaa -- judged to be of the "best quality" and are referred to as 
"gilt edge"; interest payments are protected by a large or by an 
exceptionally stable margin and principal is secure; Aa -- judged to be of 
"high quality by all standards" but as to which margins of protection or 
other elements make long-term risks appear somewhat larger than Aaa-rated 
Municipal Bonds; together with Aaa group they comprise what are generally 
known as "high grade bonds"; A -- possess many favorable investment 
attributes and are considered "upper medium grade obligations." Factors 
giving security to principal and interest A-rated Municipal Bonds are 
considered adequate, but elements may be present which suggest a 
susceptibility to impairment sometime in the future; Baa -- considered as 
medium grade obligations; i.e., they are neither highly protected nor poorly 
secured; interest payments and principal security appear adequate for the 
present but certain protective elements may be lacking or may be 
characteristically unreliable over any great length or time; Ba -- protection 
of principal and interest payments may be very moderate; judged to have 
speculative elements; their future cannot be considered as well-assured; B -- 
lack characteristics of a desirable investment; assurance of interest and 
principal payments over any long period of time may be small; Caa -- (poor 
standing; may be in default or there may be present elements of danger with 
respect to principal and interest; Ca -- speculative in a high degree; often 
in default; C -- lowest rated class of bonds; issues so rated can be regarded 
as having extremely poor prospects for ever attaining any real investment 
standing. 

   Description of Moody's ratings of state and municipal notes: Moody's 
ratings for state and municipal notes and other short-term obligations are 
designated Moody's Investment Grade ("MIG"). Symbols used will be as follows: 
MIG-1 -- Best quality, enjoying strong protection from established cash flows 
of funds for their servicing or from established and broad-based access to 
the market for refinancing, or both; MIG-2 -- High quality with margins of 
protection ample although not so large as in the preceding group. 

   Description of Moody's highest commercial paper rating: Prime-1 ("P-1") -- 
Judged to be of the best quality. Their short-term debt obligations carry the 
smallest degree of investment risk. 

   Excerpts from Standard & Poor's Corporation's Municipal Bond ratings: AAA 
- -- has the highest rating assigned by S&P; extremely strong capacity to pay 
principal and interest; AA -- has a very strong capacity to pay interest and 
repay principal and differs from the higher rated issues only in a small 
degree; A -- has a strong capacity to pay principal and interest, although 
somewhat more susceptible to the adverse changes in circumstances and 
economic conditions; BBB -- regarded as having an adequate capacity to pay 
principal and interest; normally exhibit adequate protection parameters but 
adverse economic conditions or changing circumstances are more likely to lead 
to a weakened capacity to pay principal and interest than for bonds in A 
category; BB -- B -- CCC -- CC -- predominantly speculative with respect to 
capacity to pay interest and repay principal in accordance with terms of 
obligation; BB is being paid; D-- in default, and payment of principal and/or 
interest is in arrears. 

   The ratings from "AA" to "B" may be modified by the addition of a plus or 
minus sign to show relative standing within the major rating categories. 

   Excerpt from Standard & Poor's Corporation's rating of municipal note 
issues: SP-1+ -- very strong capacity to pay principal and interest; SP-1 -- 
strong capacity to pay principal and interest. 

                                                                            B-17

<PAGE>

   Description of S&P's highest commercial papers rating: A-1+ -- This 
designation indicates the degree of safety regarding timely payment is 
overwhelming. A-1 -- This designation indicates the degree of safety 
regarding timely payment is very strong. 


B-18

<PAGE>


                   APPENDIX B--MUNICIPAL LEASE OBLIGATIONS 

   The Fund may invest in municipal lease obligations. Such securities will 
be treated as liquid under the following guidelines have been established by 
the Board of Trustees: 

       1. The obligation has been rated "investment grade" by at least on 
   NRSRO and is considered to be investment grade by the investment adviser.
 
       2. The obligation is secured by payments from a governmental lessee 
   which is generally recognized and has debt obligations which are actively 
   traded by a minimum of five broker/dealers.
 
       3. At least $25 million of the lessee debt is outstanding either in a 
   single transaction or on parity, and owned by a minimum of five 
   institutional investors.
 
       4. The investment adviser has determined that the obligation, or a 
   comparable lessee security, trades in the institutional marketplace at 
   least periodically, with a bid/offer spread of 20 basis points or less.
 
       5. The governmental lessee has a full faith and credit general 
   obligation rating of at least "A-" as published by at least one NRSRO or 
   as determined by the investment adviser. If the lessee is a state 
   government, the general obligation rating must be at least BAA1, BBB+, or 
   equivalent, as determined above.
 
       6. The projects to be financed by the obligation are determined to be 
   critical to the lessee's ability to deliver essential services.
 
       7. Specific legal features such as covenants to maintain the tax-exempt 
   status of the obligation, covenants to make lease payments without the 
   right of offset or counterclaim, covenants to return leased property to 
   the lessor in the event of non-appropriation, insurance policies, debt 
   service reserve fund, are present.
 
       8. The lease must be "triple net" (i.e.--lease payments are net of 
   property maintenance, taxes and insurance).
 
       9. If the lessor is a private entity, there must be a sale and absolute 
   assignment of rental payments to the trustee, accompanied by a legal 
   opinion from recognized bond counsel that lease payments would not be 
   considered property of the lessor's estate in the event of lessor's 
   bankruptcy. 




                                                                            B-19
<PAGE>



                                    PART C 
 
                   VANGUARD NEW YORK INSURED TAX-FREE FUND 
 
                              OTHER INFORMATION 

ITEM 24. FINANCIAL STATEMENTS AND EXHIBITS 

   (a) Financial Statements 

   
   The Registrant's audited Financial Statements for the year ended November 
30, 1995, including Price Waterhouse LLP's report thereon, are incorporated 
by reference in the Statement of Additional Information from the Registrant's 
1995 Annual Report to Shareholders which has been filed with the Commission. 
The financial statements included in the Annual Report are: 
          1. Statement of Net Assets as of November 30, 1995
          2. Statement of Operations for the year ended November 30, 1995
          3. Statement of Changes in Net Assets for the years ended November 30,
             1994 and 1995
         *4. Financial Highlights for each of the five years in the period
             ended November 30, 1995
          5. Notes to Financial Statements
          6. Report of Independent Accountants
    
- ------ 
* In addition, the financial highlights for each of the respective periods 
  presented is included in Part A of this Registration Statement. 

  (b) Exhibits
           1. Declaration of Trust**
           2. By-Laws of Registrant**
           3. Not Applicable
           4. Not Applicable
           5. Not Applicable
           6. Not Applicable
           7. Reference is made to the section entitled "Management of the Fund"
              in the Registrant's Statement of Additional Information
           8. Form of Custody Agreement**
           9. Form of Vanguard Service Agreement**
          10. Opinion of Counsel**
          11. Consent of Independent Accountants*
          12. Financial Statements--reference is made to (a) above
          13. Not Applicable
          14. Not Applicable
          15. Not Applicable
          16. Schedule for Computation of Performance Quotations*
          27. Financial Data Schedule*

- ------ 
 *Filed herewith. 
**Previously filed. 

ITEM 25. PERSONS CONTROLLED BY OR UNDER COMMON CONTROL WITH REGISTRANT 

   Registrant is not controlled by or under common control with any person. 
The Officers of the Registrant, the investment companies in The Vanguard 
Group of Investment Companies and The Vanguard Group, Inc. are identical. 
Reference is made to the caption "Management of the Fund" in the Prospectus 
constituting Part A and in the Statement of Additional Information 
constituting Part B of this Registration Statement. 
 

                                                                             C-1

<PAGE>



Item 26. Number of Holders of Securities 

   
   As of November 30, 1995 there were 19,087 shareholders of the Fund. 
    

ITEM 27. INDEMNIFICATION 

   Reference is made to Article XI of Registrant's Declaration of Trust. 

   
   Insofar as indemnification for liability arising under the Securities Act 
of 1933 may be permitted to Trustees, Officers and controlling persons of the 
registrant pursuant to the foregoing provisions, or otherwise, the registrant 
has been advised that in the opinion of the Securities and Exchange 
Commission such indemnification is against public policy as expressed in the 
Act and is, therefore, unenforceable. In the event that a claim for 
indemnification against such liabilities (other than the payment by the 
registrant of expenses incurred or paid by a Trustee, Officer or controlling 
person of the Registrant in the successful defense of any action, suit or 
proceeding) is asserted by such Trustee, Officer or controlling person in 
connection with the securities being registered, the Registrant will, unless 
in the opinion of its counsel the matter has been settled by controlling 
precedent, submit to a court of appropriate jurisdiction the question whether 
such indemnification by it is against public policy as expressed in the Act 
and will be governed by the final adjudication of such issue. 
    

ITEM 28. BUSINESS AND OTHER CONNECTIONS OF INVESTMENT ADVISER 

   Investment advisory services are provided to the Registrant on an at-cost 
basis by The Vanguard Group, Inc., a jointly-owned subsidiary of the 
Registrant and the other Funds in the Group. See the information concerning 
The Vanguard Group set forth in Parts A and B. 

ITEM 29. PRINCIPAL UNDERWRITERS 

   (a) None 

   (b) Not Applicable 

ITEM 30. LOCATION OF ACCOUNTS AND RECORDS 

   The books, accounts and other documents required by Section 31(a) under 
the Investment Company Act and the rules promulgated thereunder will be 
maintained in the physical possession of Registrant; Registrant's Transfer 
Agent, The Vanguard Group, Inc. c/o The Vanguard Financial Center, Valley 
Forge, Pennsylvania 19482; and the Registrant's Custodian, CoreStates Bank, 
N.A., Philadelphia, PA. 

ITEM 31. MANAGEMENT SERVICES 

   Other than the Amended and Restated Funds' Service Agreement with The 
Vanguard Group, Inc. which was previously filed as Exhibit 9(c) and described 
in Part B hereof under "Management of the Fund;" the Registrant is not a 
party of any management-related service contract. 

ITEM 32. UNDERTAKINGS 

   Annual meetings of shareholders will not be held except as required by the 
Investment Company Act of 1940 ("1940 Act") or other applicable law. 
Registrant undertakes to comply with the provisions of Section 16(c) of the 
1940 Act in regard to shareholders' rights to call a meeting of shareholders 
for the purpose of voting on the removal of Trustees and to assist in 
shareholder communications in such matters, to the extent required by law. 

    
  Registrant hereby undertakes to provide an Annual Report to Shareholders or 
prospective investors, free of charge, upon request. 

C-2 

<PAGE>


                                  SIGNATURES 

   
   Pursuant to the requirements of the Securities Act of 1933 and the 
Investment Company Act of 1940, the Registrant hereby certifies that it meets 
the requirements for effectiveness of this Registration Statement pursuant to 
Rule 485(b) under the Securities Act of 1933 and has duly caused this 
Post-Effective Amendment to this Registration Statement to be signed on its 
behalf by the undersigned, thereunto duly authorized, in the Town of Valley 
Forge and the Commonwealth of Pennsylvania, on the 22nd day of March, 1996. 

                                VANGUARD NEW YORK INSURED TAX-FREE FUND 
  
  
                                BY:               (SIGNATURE)
                                   ------------------------------------------- 
                                             (Raymond J. Klapinsky) 
                                                John C. Bogle*, 
                                                   Chairman 

    
Pursuant to the requirements of the Securities Act of 1933, this 
Post-Effective Amendment to the Registration Statement has been signed below 
by the following persons in the capacities and on the date indicated: 




         Signature                        Title                      Date 
 --------------------------   ------------------------------   -----------------

BY:     (SIGNATURE)           John C. Bogle*, Chairman           March 22, 1996
  -------------------------    of the Board and Trustee                       
  (Raymond J. Klapinsky)                                                   
                                                                       
BY:     (SIGNATURE)           John J. Brennan*,                  March 22, 1996 
  -------------------------    President, Chief Executive                   
  (Raymond J. Klapinsky)       Officer and Trustee                            
                                                                            
BY:     (SIGNATURE)           Barbara B. Hauptfuhrer*,           March 22, 1996 
  -------------------------   Trustee                                          
  (Raymond J. Klapinsky)                                                      
                                                                             
BY:     (SIGNATURE)           John C. Sawhill*,                  March 22, 1996
   ------------------------    Trustee                                         
  (Raymond J. Klapinsky)                                                    
                                                                             
BY:     (SIGNATURE)           Robert E. Cawthorn*,               March 22, 1996
  -------------------------    Trustee                                         
  (Raymond J. Klapinsky)                                                       
                                                                               
                                                                            
BY:     (SIGNATURE)           Alfred M. Rankin, Jr.*,            March 22, 1996
  -------------------------    Trustee                                       
  (Raymond J. Klapinsky)                                                      
                                                                          
                                                                         
BY:     (SIGNATURE)           Burton G. Malkiel*,                March 22, 1996
  -------------------------    Trustee                                        
  (Raymond J. Klapinsky)                                                    
                                                                          
BY:     (SIGNATURE)           James O. Welch, Jr.*,              March 22, 1996
  -------------------------    Trustee                                        
  (Raymond J. Klapinsky)                                                  
                                                                             
BY:     (SIGNATURE)           J. Lawrence Wilson*,               March 22, 1996
  -------------------------    Trustee                                        
  (Raymond J. Klapinsky)                                                       
                                                                              
BY:       (SIGNATURE)         Richard F. Hyland*,                March 22, 1996
  -------------------------    Treasurer and  Principal                       
  (Raymond J. Klapinsky)       Financial  Officer and Accounting               
                               Officer                                         
                                                                               
                              
    

- ------ 
* By Power of Attorney--See File Number 2-14336, January 23, 1990. 
  Incorporated by Reference. 


<PAGE>


                              INDEX TO EXHIBITS 

Consent of Independent Accountants ...................................EX-99.B11 
Schedule for Computation of Performance Quotations ...................EX-99.B16 
Financial Data Schedule ..............................................    EX-27 
 






                                                                     EX-99.B11 


                      CONSENT OF INDEPENDENT ACCOUNTANTS 

   We hereby consent to the incorporation by reference in the Prospectus and 
Statement of Additional Information, constituting parts of this amended 
Registration Statement on Form N-1A, of our report dated December 29, 1995, 
relating to the financial statements and financial highlights, appearing in 
the November 30, 1995 Annual Report to Shareholders of Vanguard New York 
Insured Tax-Free Fund. We also consent to the references to us under the 
headings "Financial Highlights" and "General Information" in the Prospectus 
and "Financial Statements" in the Statement of Additional Information. 

 
PRICE WATERHOUSE LLP 
 
Philadelphia, PA 
March 21, 1996 
 




                                                                     EX-99.B16 


              SCHEDULE FOR COMPUTATION OF PERFORMANCE QUOTATIONS 
                   VANGUARD NEW YORK INSURED TAX-FREE FUND 

1. Average Annual Total Return (As of November 30, 1995) 
    
     P (1 + T)(n) = ERV 
    
   Where:   P = a hypothetical initial payment of $1,000 
             
            T = average annual total return 
             
            N = number of years 
             
          ERV = ending redeemable value at the end of the period 
    
   EXAMPLE: 
   One Year 
    
            P = $1,000.00
    
            T = +19.90%
    
            N = 1
    
          ERV = $1,199.00
  
   Five Year 
    
            P = $1,000.00
    
            T = +9.13%
    
            N = 5
    
          ERV = $1,548.05
    
   Ten Year 
    
            P = $1,000.00
    
            T = +7.65%*
    
            N = *
    
          ERV = $2,036.40*
    
*Since inception on April 7, 1986 

2. YIELD (30 Days Ended November 30, 1995) 
    
   Yield = 2 [(a - b     (6)
             -------  + 1) - 1] 
             [ c X d  
    
   ------ 
    
   
    
   Where:  a = dividends and interest paid during the period 
            
           b = expense dollars during the period (net of reimbursements) 
            
           c = the average daily number of shares outstanding during the 
               period 
            
           d = the maximum offering price per share on the last day of the 
               period 
            
   Example a = $3,587,525.07 
    
           b = $113,245.00
           c = 77,412,932.320 
    
           d = $10.95 
 
       Yield = 4.97% 
 


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<NAME> VANGUARD NEW YORK INSURED TAX-FREE FUND
<MULTIPLIER> 1,000
<CURRENCY> US
<PERIOD-TYPE>                   YEAR
<FISCAL-YEAR-END>                          NOV-30-1995
<PERIOD-START>                             DEC-01-1995
<PERIOD-END>                               NOV-30-1995
<EXCHANGE-RATE>                                      1
<INVESTMENTS-AT-COST>                          803,129
<INVESTMENTS-AT-VALUE>                         861,577
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<EQUALIZATION>                                       0
<DISTRIBUTIONS-OF-INCOME>                       42,840
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