VANGUARD NEW YORK INSURED TAX FREE FUND
N-30D, 1994-07-28
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<PAGE>   1

CHAIRMAN'S LETTER

DEAR SHAREHOLDER:

     The six months ended May 31, the first half of the 1994 fiscal year
for the eleven Portfolios of the Vanguard State Tax- Free Funds, witnessed
something that we have not seen much of since 1987: rising interest rates. As a
result, the prices of long- term municipal bonds declined during the period,
while the income from money market instruments received a nice boost.

     This environment, of course, negatively impacted the net asset values
of each of our Insured Long-Term Portfolios, as reflected in the table on page
2. (The net asset values of our Money Market Portfolios, as you would expect,
remained constant, at $1.00 per share.) While fluctuating asset values are part
and parcel of bond investing, our Long-Term Portfolios exceeded the total
returns (capital change plus income) achieved by competitive state tax-free
bond funds. What is more, all of our Portfolios remain virtually peerless in
the mutual fund field with respect to their investment quality, as shown in the
third column of the table on page 2. In summary form, here are the Portfolio
highlights over the past twelve months:

*   THE STATE MONEY MARKET PORTFOLIOS--provided total returns ranging from
+2.2% to +2.3% . . . current yields are in the area of 2.6%, about the same
as they were twelve months ago but nicely above their level at the outset
of the fiscal half year . . . net asset values remained at $1.00 per share.

*   THE STATE INSURED LONG-TERM PORTFOLIOS--reflecting the rebound in interest
rates, turned in modest total returns ranging from +1.9% to +3.3% . . .
current income yields are running about 5.4%, some 40 basis points (0.40%)
higher than they were twelve months ago.

     The detailed results for each of our State Tax-Free
Portfolios--including per share net asset values, dividends, and capital gains
distributions, as well as current yields--are presented on the following page.
To provide some perspective on how our Insured Long-Term Portfolios fared in
the face of rising interest rates, the table that follows summarizes the income
returns and the capital returns for each Portfolio:

<TABLE>
<CAPTION>
- - ----------------------------------------------------------------------------
                                            Investment Returns
                                           Twelve Months Ended
                                               May 31, 1994                 
Insured Long-Term             ----------------------------------------------
Portfolio*                     Income            Capital             Total
- - ----------------------------------------------------------------------------
<S>                             <C>               <C>                <C>
CALIFORNIA                      +5.4%             -3.5%              +1.9%
NEW YORK                        +5.4              -3.2               +2.2
PENNSYLVANIA                    +5.6              -2.3               +3.3
NEW JERSEY                      +5.3              -3.4               +1.9
OHIO                            +5.2              -2.8               +2.4
FLORIDA                         +5.1              -2.2               +2.9
- - ----------------------------------------------------------------------------
</TABLE>

*  On March 4, 1994, the California Insured Intermediate-Term Portfolio was
   introduced. Since its inception, the Portfolio has achieved an income return
   of +1.0%, a capital return of +0.4%, and a total return of +1.4%.

*  FIXED-INCOME MARKET REVIEW
The basic benchmark for the bond market is the long-term U.S. Treasury bond.
During the past six months, its yield rose from 6.3% at the start of the period
to 7.4% at its conclusion. This yield change engendered a decline of about -13%
in the Treasury bond's price. I am happy to report that the tax-exempt bond
market fared a good bit better, with the yield on long-term high-grade
municipal bonds rising from 5.5% to 6.1%, resulting in a price decline of some
- - -8%. However painful this decline may be for investors in long-term bonds, it
is worth noting that interest rates had been dropping steadily for some seven
years, and the retracement during the past six months has merely returned rates
to the level prevailing at the end of 1992.

     A primary cause of the interest rate rise was investor fears about a
resurgence of inflation. So far, at least, there is little evidence of it. The
U.S. Consumer Price Index has risen just 2.3% over the past twelve months,
although more sensitive indicators--such as commodity prices--have been rising
at a much higher rate. In an effort to quell these inflationary fears, the
Federal Reserve acted to "tighten" the money supply and slow economic growth
and potential future inflation, raising the


                                      1

<PAGE>   2

Federal funds rate (at which banks borrow from one another) four times--in
February, March, April, and again in May--from 3.00% to 4.25%.

     These increases in short-term rates are often seen by market participants
as a restraint on potential inflation, and thus cause long-term rates to fall.
This time around, quite the reverse has been true. In any event, proving that
"it is an ill wind (indeed) that blows no good," the rate increase has added to
the income received by investors in our Money Market Portfolios. And, because
of the "lag" from the date interest rates rise until they are fully manifested
in money market fund yields, further dividend increases in our Money Market
Portfolios likely lie in prospect.

*  IN SUMMARY
In my Chairman's letter to you one year ago, I noted that "it is hard to
imagine that the steady trend toward ever-lower interest rates can go much
further." I went on to caution that if rates did reverse their decline in
response to a strengthening economy, the capital rewards enjoyed by our
longer-term Portfolios would turn to capital penalties. While I do not presume
any forecasting ability whatsoever, these observations have proved prescient.
Nonetheless, provided that you own the Vanguard Portfolio (or combination of
Portfolios) that meets your long-term risk-reward objectives, I would urge you
to "stay the course" and avoid the temptation to make precipitate changes in
your fund holdings.

     I look forward to reporting on our results for the full 1994 fiscal year
six months hence.

Sincerely,



/s/JOHN C. BOGLE
- - ----------------
John C. Bogle
Chairman of the Board

June 17, 1994

<TABLE>
<CAPTION>
                                                                 Net Asset Value
                               Total                                Per Share             Dividends       Total Return
                          Net Assets                            ------------------    -----------------  ---------------
                          (millions)    Average    Average      Nov. 30,   May 31,     Six      Twelve    Six     Twelve    Current
Portfolio               May 31, 1994    Maturity   Quality*        1993      1994     Months    Months   Months   Months     Yield**
- - ------------------------------------------------------------------------------------------------------------------------------------
<S>                        <C>        <C>            <C>        <C>        <C>        <C>        <C>        <C>      <C>       <C>
MONEY MARKET
  CALIFORNIA  . . . . .    $1,126        35 DAYS     MIG 1      $  1.00    $  1.00    $ .011      $.023     +1.1%    +2.3%     2.55%
  PENNSYLVANIA  . . . .     1,041        37 DAYS     MIG 1         1.00       1.00      .011       .023     +1.1     +2.3      2.60
  NEW JERSEY  . . . . .       803        41 DAYS     MIG 1         1.00       1.00      .011       .022     +1.1     +2.2      2.46
  OHIO  . . . . . . . .       139        47 DAYS     MIG 1         1.00       1.00      .011       .023     +1.2     +2.3      2.57
- - ------------------------------------------------------------------------------------------------------------------------------------
INSURED LONG-TERM
  CALIFORNIA  . . . . .    $  929     12.9 YEARS       Aaa      $ 11.30    $ 10.66    $ .451+     $.753+    -1.8%    +1.9%     5.58%
  CALIFORNIA INTERMEDIATE-
    TERM  . . . . . . .        57      5.3 YEARS       Aaa           --      10.04      .101++       --     +1.4++     --      4.82
  NEW YORK  . . . . . .       760     11.8 YEARS       Aaa        10.97      10.49      .306+      .602+    -1.6     +2.2      5.41
  PENNSYLVANIA  . . . .     1,430     11.7 YEARS       Aaa        11.36      10.85      .388+      .703+    -1.1     +3.3      5.47
  NEW JERSEY  . . . . .       700     11.5 YEARS       Aaa        11.77      11.18      .374+      .690+    -1.9     +1.9      5.41
  OHIO  . . . . . . . .       162      9.7 YEARS       Aaa        11.61      11.08      .327+      .630+    -1.8     +2.4      5.48
  FLORIDA . . . . . . .       292     12.1 YEARS       Aaa        10.86      10.38      .339+      .611+    -1.3     +2.9      5.39
- - ------------------------------------------------------------------------------------------------------------------------------------
</TABLE>
  *  MIG 1 and Aaa are Moody's highest ratings for, respectively, short-term
     and long-term municipal bonds.
**   Money Market Portfolios' yields are 7-day annualized yields; others are
     30-day SEC yields.
 +   Include capital gains distributions of $.152 for California, $.012 for New
     York, $.079 for Pennsylvania, $.063 for New Jersey, $.032 for Ohio, and
     $.070 for Florida.
++   Since inception, March 4, 1994.
     The shares of each of the Vanguard "single state" Portfolios are available
     for purchase solely by residents of the designated states.





                                       2
<PAGE>   3

AVERAGE ANNUAL TOTAL RETURNS

THE CURRENT YIELDS NOTED IN THE CHAIRMAN'S LETTER ARE CALCULATED IN ACCORDANCE
WITH SEC GUIDELINES. THE AVERAGE ANNUAL TOTAL RETURNS FOR THE PORTFOLIOS
(PERIODS ENDED MARCH 31, 1994) ARE AS FOLLOWS:

<TABLE>
<CAPTION>
                                                  INCEPTION                                         SINCE
PORTFOLIO                                           DATE            1 YEAR        5 YEARS         INCEPTION
- - ------------------------------------              ---------         ------        -------         ---------
<S>                                               <C>               <C>            <C>              <C>
CALIFORNIA INSURED LONG-TERM                       4/7/86           +1.77%         +8.56%           +7.70%
CALIFORNIA INSURED INTERMEDIATE-TERM               3/4/94             --             --             -0.64
CALIFORNIA MONEY MARKET                            6/1/87           +2.34          +4.05            +4.34
NEW YORK INSURED TAX-FREE                          4/7/86           +2.37          +8.97            +7.23
PENNSYLVANIA INSURED LONG-TERM                     4/7/86           +3.14          +9.22            +8.11
PENNSYLVANIA MONEY MARKET                         6/13/88           +2.31          +4.15            +4.39
NEW JERSEY INSURED LONG-TERM                       2/3/88           +2.44          +8.87            +8.65
NEW JERSEY MONEY MARKET                            2/3/88           +2.24          +4.12            +4.37
OHIO INSURED LONG-TERM                            6/18/90           +2.70            --             +9.12
OHIO MONEY MARKET                                 6/18/90           +2.31            --             +3.54
FLORIDA INSURED TAX-FREE                           9/1/92           +2.56            --             +7.01
</TABLE>

THESE DATA REPRESENT PAST PERFORMANCE. THE INVESTMENT RETURN AND PRINCIPAL
VALUE OF AN INVESTMENT WILL FLUCTUATE SO THAT AN INVESTOR'S SHARES, WHEN
REDEEMED, MAY BE WORTH MORE OR LESS THAN THEIR ORIGINAL COST.

PLEASE NOTE THAT AN INVESTMENT IN A MONEY MARKET FUND, SUCH AS A MONEY MARKET
PORTFOLIO OF THE VANGUARD STATE TAX-FREE FUNDS, IS NEITHER INSURED NOR
GUARANTEED BY THE U.S. GOVERNMENT, AND THERE IS NO ASSURANCE THAT THE FUND WILL
BE ABLE TO MAINTAIN A STABLE NET ASSET VALUE OF $1.00 PER SHARE.





                                       3
<PAGE>   4
REPORT FROM THE INVESTMENT ADVISER

STATE INSURED
LONG-TERM PORTFOLIOS

Over the past six months, the pace of domestic economic activity accelerated
sharply. Strong improvements in the rate of growth in Gross Domestic Product
(GDP), and a host of related statistics such as home sales, automobile sales,
and consumer confidence, provided ample evidence of renewed vigor. Bond markets
seldom react well to strong economic signals and this period was no exception.
The yield on the 30-year Treasury bond rose 1.1 percentage points (from 6.3% to
7.4%). During the same period, municipal bonds performed slightly better, with
the yield on long-term high-grades rising 0.6% (from 5.5% to 6.1%), producing
an 8.3% loss of value.

     As one would expect, the sharp rise in interest rates negatively impacted
the share price of the State Insured Long-Term Portfolios. To be sure, a
decline of this nature can be disconcerting to even the most resolute long-term
investor. However, following more than a decade of exceptional returns of
longer-term fixed-income assets, the poor six-month period represents only a
partial "give back" of previous prosperity. Looking beyond the short-term share
price volatility, a shareholder of the State Insured Long-Term Portfolios can
expect to receive an attractive, consistent, and durable stream of tax-exempt
dividend income.

* SUCCESSFUL STRATEGIES . . .
For the recent period, two of several core strategies stand out for enhancing
the relative returns of the State Insured Long-Term Portfolios. First, a
reduction in average maturity over the past year improved relative market
performance and moderated some of the "sting" of a bear market. Some of this
was accomplished by focusing on municipals maturing in 15 to 20 years, rather
than the slightly higher yielding but more volatile 30-year maturities. This
modest reduction in average maturity effectively "locked-in" a portion of the
gains in share price achieved in the previous bull market.

     Second, the prudent maintenance of reserve positions of about 10% of fund
assets added to our relative stability. What is more, these reserves provided a
liquidity cushion to meet shareholder redemptions. In good times, reserves
(which normally yield less than longer-term assets) forego a small amount of
yield potential. In difficult market conditions, such as prevailed during the
past six months, the additional reserves allow the portfolio to meet redemption
requests without the inopportune (and sometimes "distressed") sale of
securities.

* LOOKING FORWARD . . .
The issuance of new municipal bonds has fallen dramatically. Issuance for the
first six months in fiscal 1994 was 26% below the pace of a year earlier. Early
indications show forward supply even lower compared to the "mad dash" of 1993.
Municipalities appear to have completed the process of refinancing older,
higher coupon debt of the 1980's and early 1990's. At the same time, a record
number of previously mentioned high coupon bonds are approaching their call
dates, and a huge amount of principal will be returned to owners of individual
bonds. All things being equal, this should continue to provide more attractive
returns for municipal bonds than their taxable brethren.

     In conclusion, it would be reassuring to believe that the recent increase
in interest rates is sufficient to "rein in" the rapidly expanding U.S. economy
and dampen any inflationary expectations. Yet, that observation might be
premature. If history serves as any guide, the process may take longer than the
recent six months of "pain." If so, there could be more share price
unpleasantness ahead before the markets resume their positive return pattern of
the past decade. However, attempting to "time" the turnaround--getting out at
the highs and then getting back in at the lows--tends to be equally futile for
the institutional and individual investor alike. The best advice we know is to
endure the swings and allow the powerful tax exempt compounding of interest to
continue.


                                       4

<PAGE>   5

STATE MONEY MARKET PORTFOLIOS

The past six months ushered in a change in the Federal Reserve Board's
previously accommodative monetary policy. Since February 4, 1994, market
participants watched anxiously as the Federal Reserve Board, in four separate
instances, pushed the Federal funds rate up 125 basis points (1.25%) to 4.25%
and tightened the discount rate 50 basis points (0.50%) to 3.50%. This series
of moves by the Fed has signaled the end of stimulative policy (maintained
throughout 1993) and the initiation of a policy of "neutrality."

     The effect of the tightening on the short-term municipal market was
surprisingly mild. While yields on "first tier" taxable money market funds rose
approximately 70 basis points over the six-month period, yields on
state-specific and general purpose tax- free money funds rose a mere 35 basis
points. The primary contributor to the unresponsive municipal market was the
scarcity of new issue supply. Supply of short-term municipal securities is
quite cyclical, and depends on an issuer's fiscal year, which generally runs
from July 1 to June 30. As a result, supply typically remains light in the
months leading up to June and dramatically increases in the summer months, as
issuers prepare to fund their upcoming budgetary needs in the new fiscal year.
This lack of supply experienced during a period of rising rates in the broader
taxable markets enabled short-term municipal yields to maintain relative
stability. As technical supply factors temporarily have been depressing yields
on short-term municipal securities, we have been targeting a low average
weighted maturity for the tax-exempt money funds of 45 to 60 days. Our
Portfolios should be commensurately more responsive when new issue supply
surges and interest rates rise. We expect the shift from scarcity to abundance
will occur within weeks.

     While the market focused on an accelerating economy and the rise in
interest rates, the Securities and Exchange Commission quietly launched its own
initiative to ensure the net asset value safety of tax-exempt money funds,
consistent with those already applicable to taxable money funds. In fact, the
SEC has proposed regulations that coincide with (or in some cases are less
restrictive than) our conservative approach to managing money market funds.
Thus, they will have little impact on the Vanguard Money Market Portfolios. We
believe that the Commission's proposals, if adopted, will be a positive force
in elevating industrywide portfolio standards.

     In conclusion, the upcoming months could potentially bring about
significant regulatory and economic changes in our market.  While keeping a
watchful eye on the actions of the Federal Reserve Board and maintaining our
conservative investment approach, we look forward to capitalizing on any
opportunities that may result.

Sincerely,

Ian A. MacKinnon
Senior Vice President

Jerome J. Jacobs
Vice President

Pamela E. Wisehaupt
Vice President

David E. Hamlin
Assistant Vice President

Reid O. Smith
Assistant Vice President

Danine A. Mueller
Portfolio Manager

Vanguard Fixed Income Group

June 13, 1994


                                       5

<PAGE>   6

STATEMENT OF NET ASSETS
                                                FINANCIAL STATEMENTS (unaudited)
                                                                    May 31, 1994


<TABLE>
<CAPTION>
                                                  Face                         Market
                                                Amount                          Value
                                                 (000)                         (000)+
- - -------------------------------------------------------------------------------------
MUNICIPAL BONDS (97.7%)                      
- - -------------------------------------------------------------------------------------
<S>                                          <C>                            <C>
ISSUER INSURED (80.6%)                       
  Albany County Civic Center GO              
     6.60%, 6/1/96 (3) (Prere.)              $     630                      $     669
  Albany County GO                           
     7.00%, 1/15/05 (2)                          1,250                          1,385
     5.00%, 10/1/05 (3)                          2,000                          1,952
     5.00%, 10/1/06 (3)                          3,150                          3,035
     5.00%, 10/1/12 (3)                          4,400                          3,955
  Albany Municipal Water Finance Auth.       
     7.50%, 12/1/17 (1)                          2,080                          2,296
     5.50%, 12/1/22 (3)                          4,500                          4,103
  Babylon Waste Water Facilities GO          
     9.00%, 8/1/08 (3)                           4,900                          6,468
     9.00%, 8/1/09 (3)                           2,800                          3,719
     9.00%, 8/1/10 (3)                           4,900                          6,555
  Broome County Public Safety                
    Facility Project                         
     5.25%, 4/1/15 (1)                           3,000                          2,685
  Buffalo General Improvement                
     6.75%, 3/1/06 (1)                           1,815                          1,963
     6.75%, 3/1/07 (1)                             390                            420
     6.75%, 3/1/09 (1)                             410                            438
     6.75%, 3/1/10 (1)                             380                            405
     6.75%, 3/1/11 (1)                             385                            408
  Buffalo GO                                 
     3.25%, 4/1/95 (1)                           2,750                          2,742
  Buffalo Municipal Water                    
  Finance Auth.                              
     5.75%, 7/1/19 (4)                           7,450                          7,071
  Buffalo Sewer System Rev.                  
     7.625%, 7/1/96 (2) (Prere.)                 1,000                          1,091
     5.25%, 7/1/08 (3)                           3,500                          3,316
     5.00%, 7/1/12 (3)                           2,400                          2,135
  Clifton Park Water Auth.                   
     6.375%, 10/1/02 (3) (Prere.)                3,500                          3,821
  Duchess County Resource Recovery           
     7.50%, 1/1/09 (3)                           2,000                          2,236
  Erie County GO                             
     10.00%, 2/1/95 (3)                          4,445                          4,629
     6.10%, 1/15/06 (3)                          1,865                          1,957
     6.125%, 1/15/07 (3)                         1,660                          1,734
     6.125%, 1/15/09 (3)                           735                            763
     6.125%, 1/15/10 (3)                           735                            759
     6.125%, 1/15/11 (3)                           735                            756
     6.125%, 1/15/12 (3)                           735                            756
  Erie County Water Auth.                    
     5.00%, 12/1/04 (2)                          5,920                          5,872
     0.00%, 12/1/05 (2)                          3,000                          1,598
     0.00%, 12/1/06 (2)                          6,915                          3,327
     6.00%, 12/1/08 (2)                          1,600                          1,636
  Huntington GO                              
     6.70%, 2/1/10 (3)                             375                            408
     6.70%, 2/1/11 (3)                             310                            337
     5.50%, 4/1/13 (3)                           3,400                          3,187
  City of Jamestown GO                       
     7.50%, 5/15/02 (2)                            110                            127
     7.50%, 5/15/06 (2)                            250                            293
  Metropolitan Transit Auth.                 
     of New York                             
     (Commuter Facilities Rev.)              
     6.10%, 7/1/09 (1)                           6,035                          6,203
     5.50%, 7/1/17 (1)                           2,500                          2,298
     (Transportation Facilities Rev.)        
     5.40%, 7/1/07 (3)                          17,330                         17,042
     7.00%, 7/1/09 (2)                           5,650                          6,289
     6.375%, 7/1/10 (3)                          6,100                          6,327
     6.00%, 7/1/11 (2)                           2,000                          2,001
  Monroe County GO                           
     (Rochester Water Dist.)                 
     5.60%, 6/1/04 (3)                           1,235                          1,262
     5.70%, 6/1/05 (3)                           1,350                          1,382
     5.80%, 6/1/06 (3)                           1,340                          1,374
     5.90%, 2/1/07 (3)                             550                            564
  Montgomery, Ostego, Scholoharie            
     Counties Solid Waste                    
     5.25%, 1/1/14 (1)                           1,640                          1,480
  Mount Sinai Union Free                     
     School Dist.                            
     6.20%, 2/15/14 (2)                          1,050                          1,095
     6.20%, 2/15/15 (2)                            540                            562
  Nassau County Combined                     
     Sewer Dist. GO                          
     4.70%, 10/1/04 (3)                          1,805                          1,696
     4.80%, 10/1/05 (3)                          1,760                          1,656
     4.90%, 10/1/06 (3)                          1,740                          1,638
     6.20%, 5/15/07 (1)                            840                            880
     5.00%, 10/1/07 (3)                          1,715                          1,618
     6.20%, 5/15/08 (1)                            835                            874
     5.35%, 7/1/08 (1)                           4,730                          4,575
     5.00%, 10/1/08 (3)                          1,695                          1,589
     5.35%, 1/15/09 (1)                          3,505                          3,364
     6.25%, 5/15/09 (1)                            825                            863
     5.35%, 7/1/09 (1)                           4,635                          4,454
     6.25%, 5/15/10 (1)                            820                            856
  Nassau County GO                           
     TOB VRDO 2.8%, 6/15/94 (1)                    205                            205
     TOB VRDO 2.8%, 7/1/94 (1)                   2,720                          2,720
     5.50%, 7/15/07 (1)                          1,270                          1,261
     5.50%, 7/15/08 (1)                          1,300                          1,276
     5.00%, 5/1/09 (3)                           3,210                          2,959
     5.50%, 7/15/09 (1)                          1,325                          1,290
     5.00%, 5/1/10 (3)                           2,875                          2,630
     5.75%, 5/15/10 (3)                            670                            667
</TABLE>                                     
                                       6
<PAGE>   7
<TABLE>
<CAPTION>
                                                 Face                         Market
                                               Amount                          Value
                                                (000)                         (000)+
- - ------------------------------------------------------------------------------------
  <S>                                        <C>                            <C>
     5.50%, 7/15/10 (1)                      $  1,345                       $  1,302
     5.75%, 8/1/10 (3)                            845                            845
     5.75%, 2/1/11 (1)                          1,100                          1,092
     5.00%, 5/1/11 (3)                          1,770                          1,599
     5.50%, 7/15/11 (1)                         1,370                          1,313
     5.00%, 5/1/12 (3)                          1,760                          1,577
     5.875%, 8/1/12 (3)                           825                            820
  New York City Cultural Resources           
     (Museum of Modern Art)                  
     5.40%, 1/1/06 (2)                            805                            799
     5.50%, 1/1/07 (2)                            840                            834
     5.40%, 1/1/12 (2)                          1,400                          1,315
  New York City GO                           
     5.75%, 8/1/09 (3)                          4,250                          4,190
     6.625%, 8/1/13 (1)                        13,500                         14,734
  New York City Health &                     
     Hosp. Corp.                             
     5.625%, 2/15/13 (2)                       23,400                         22,168
  New York City Water &                      
     Sewer Auth.                             
     VRDO 2.9%, 6/1/94 (3)                      7,900                          7,900
     6.75%, 6/15/99 (3) (Prere.)                3,385                          3,689
     5.875%, 6/15/12 (2)                       20,000                         19,639
     5.875%, 6/15/13 (2)                       20,000                         19,519
     6.75%, 6/15/14 (3)                         1,615                          1,676
     6.00%, 6/15/16 (3)                         4,000                          3,933
     5.375%, 6/15/19 (2)                        5,250                          4,684
  New York State Dormitory Auth.             
     (City Univ. of New York)                
     6.50%, 7/1/08 (3)                          5,545                          5,931
     5.75%, 7/1/11 (3)                          5,950                          5,798
     7.00%, 7/1/14 (3)                         20,700                         22,194
     (Colgate Univ.)                         
     6.50%, 7/1/21 (1)                          1,350                          1,385
     (Fashion Institute Student              
     Housing Corp.)                          
     7.10%, 7/1/03 (1)                            590                            630
     7.20%, 7/1/05 (1)                          1,705                          1,816
     7.20%, 7/1/06 (1)                          1,855                          1,975
     (Fordham Univ.)                         
     7.20%, 7/1/15 (2)                          4,500                          4,958
     (Foundling Charities Corp.)             
     6.50%, 7/1/12 (1)                          6,530                          6,712
     (Iona College)                          
     7.625%, 7/1/09 (1)                         5,000                          5,506
     (Ithaca College)                        
     6.25%, 7/1/21 (1)                          7,500                          7,572
     (Mt. Sinai School of Medicine)          
     8.375%, 7/1/95 (3) (Prere.)                  650                            693
     5.00%, 7/1/15 (1)                          3,000                          2,602
     6.75%, 7/1/15 (1)                          7,245                          7,585
     (New York Public Library)               
     0.00%, 7/1/06 (1)                            910                            449
     0.00%, 7/1/07 (1)                          1,000                            458
     0.00%, 7/1/08 (1)                            910                            386
     0.00%, 7/1/09 (1)                            910                            357
     0.00%, 7/1/10 (1)                            500                            184
     0.00%, 7/1/11 (1)                            500                            172
     (New York Univ.)                        
     6.70%, 7/1/96 (1) (Prere.)                 1,250                          1,331
     6.00%, 7/1/15 (3)                         32,165                         31,897
     (Rensselaer Polytech. Inst.)            
     6.50%, 7/1/06 (3)                          3,000                          3,194
     (Siena College)                         
     6.00%, 7/1/11 (1)                          1,500                          1,504
     (Special Act)                           
     6.00%, 7/1/15 (3)                          2,675                          2,653
     (Union College)                         
     5.75%, 7/1/10 (3)                          1,800                          1,792
  New York State Energy                      
     Research & Development                  
     Auth. PCR                               
     (Niagara Mohawk)                        
     6.625%, 10/1/13 (3)                       10,000                         10,426
  New York State Medical Care Facility       
     Finance Agency                          
     (Beth Israel Medical Center)            
     5.00%, 11/1/13 (1)                         4,750                          4,180
     (Columbia Presbyterian Hosp.)           
     9.75%, 1/15/95 (8) (Prere.)                8,400                          8,948
     (Mental Health Services)                
     7.40%, 2/15/99 (1) (Prere.)                1,660                          1,852
     7.40%, 8/15/07 (1)                           890                            974
     5.50%, 8/15/21 (3)                         8,000                          7,287
     (St. Mary's Hosp.)                      
     8.375%, 11/1/14 (2) (Prere.)               2,200                          2,375
     (Sisters of Charity--Buffalo)           
     6.625%, 11/1/18 (2)                        5,500                          5,694
  New York State Power Auth.                 
     7.30%, 1/1/96 (3) (Prere.)                 3,405                          3,636
  New York State Thruway Auth.               
     3.40%, 1/1/95 (3)                          2,000                          1,997
     3.40%, 3/1/95 (3)                          4,000                          3,993
     5.00%, 1/1/14 (1)                          3,000                          2,635
     5.50%, 1/1/23 (3)                          6,800                          6,191
  New York State Urban                       
     Development Corp.                       
     5.375%, 1/1/12 (1)                        14,000                         13,057
  Niagara Falls Bridge Comm.                 
     5.25%, 10/1/15 (3)                         5,000                          4,513
     6.25%, 10/1/20 (3)                         8,685                          9,100
     6.25%, 10/1/21 (3)                         9,230                          9,678
  North Hempstead GO                         
     6.30%, 4/1/08 (3)                          2,055                          2,187
     6.40%, 4/1/10 (3)                          1,500                          1,586
     6.40%, 4/1/11 (3)                          2,075                          2,189
</TABLE>

                                       7
<PAGE>   8
STATEMENT OF NET ASSETS (continued)

<TABLE>
<CAPTION>
                                                 Face                         Market
                                               Amount                          Value
                                                (000)                         (000)+
- - ------------------------------------------------------------------------------------
<S>                                          <C>                            <C>
  North Hempstead Solid Waste Auth.          
     5.00%, 2/1/12 (1)                       $  3,370                       $  3,002
  Oyster Bay Public Improvement              
     5.40%, 2/15/03 (1)                         1,475                          1,495
     5.60%, 2/15/05 (1)                         1,000                          1,023
     5.70%, 2/15/07 (1)                           805                            819
     5.70%, 2/15/09 (1)                           980                            979
     5.70%, 2/15/11 (1)                           300                            295
  Rochester GO                               
     5.70%, 8/15/02 (2)                         2,340                          2,460
     5.70%, 8/15/03 (2)                         2,330                          2,442
     5.70%, 8/15/04 (2)                         2,180                          2,274
  Town of Smithtown                          
     5.25%, 4/1/06 (1)                          1,000                            996
     5.45%, 4/1/08 (1)                            400                            394
  Suffolk County GO                          
     5.00%, 4/1/06 (1)                          2,255                          2,192
     5.00%, 7/15/06 (3)                         1,000                            968
     5.10%, 7/15/07 (3)                         1,280                          1,230
     5.20%, 7/15/08 (3)                         1,100                          1,056
  Suffolk County Southwest                   
     Sewer Dist. GO                          
     6.40%, 2/1/03 (3)                          1,190                          1,239
     6.00%, 2/1/07 (3)                          5,000                          5,115
     6.00%, 2/1/08 (3)                          5,000                          5,093
  Suffolk County Water Auth.                 
     5.75%, 6/1/02 (2) (Prere.)                 1,100                          1,157
     5.10%, 6/1/07 (1)                          7,110                          6,785
     5.25%, 6/1/10 (2) (ETM)                    3,790                          3,620
     5.25%, 6/1/11 (2) (ETM)                    2,380                          2,254
     5.25%, 6/1/12 (2) (ETM)                    4,290                          4,047
     5.75%, 6/1/13 (2)                          7,340                          7,150
     5.25%, 6/1/17 (2) (Prere.)                21,305                         21,060
     5.25%, 6/1/17 (2)                          1,695                          1,539
  Triborough Bridge & Tunnel Auth.           
     5.50%, 1/1/17 (2)                         18,485                         17,049
OUTSIDE NEW YORK:                            
  Puerto Rico Public Building Auth.          
     0.00%, 7/1/03 (3)                          4,000                          2,439
                                                                            --------
           GROUP TOTAL                                                       611,989
                                                                            --------
- - ------------------------------------------------------------------------------------
PORTFOLIO INSURED (1.2%)                     
  New York State Dormitory Auth.             
     (Cornell Univ.)                         
     6.875%, 7/1/14                             6,825                          7,220
  New York State Energy                      
     Resources Auth.                         
     (Niagara Mohawk Power Corp.)            
     8.875%, 11/1/25                            1,100                          1,184
  Port Auth. of New York & New Jersey        
     8.70%, 7/15/20                               750                            804
                                                                            --------
           GROUP TOTAL                                                         9,208
                                                                            --------
- - ------------------------------------------------------------------------------------
SECONDARY MARKET INSURED (7.2%)              
  Municipal Assistance Corp. for             
     New York City                           
     6.00%, 7/1/08 (3)                         22,350                         22,592
  New York City Water & Sewer                
     Auth. Rev.                              
     5.00%, 6/15/17 (3)                         4,000                          3,340
  New York State Dormitory Auth.             
     (City Univ. of New York)                
     5.75%, 7/1/09 (3)                          5,000                          4,970
     (Cornell Univ.)                         
     7.25%, 7/1/12 (1)                          1,175                          1,290
     (State Univ.)                           
     7.25%, 5/15/00 (2) (Prere.)                  500                            566
     6.00%, 5/15/17 (2)                         5,600                          5,586
  Port Auth. of New York &                   
     New Jersey                              
     6.50%, 1/15/26 (1)                         1,500                          1,540
  Triborough Bridge & Tunnel Auth.           
     6.75%, 1/1/09 (2)                          3,000                          3,272
     6.875%, 1/1/15 (3)                         7,000                          7,377
     5.00%, 1/1/17 (2)                            105                             90
     5.00%, 1/1/17 (3)                            395                            338
     5.50%, 1/1/19 (2)                          4,000                          3,644
                                                                            --------
           GROUP TOTAL                                                        54,605
                                                                            --------
- - ------------------------------------------------------------------------------------
NON-INSURED (8.7%)                           
  Municipal Assistance Corp.                 
     for New York City                       
     9.00%, 7/1/95 (Prere.)                     2,350                          2,522
  New York City Trust for Cultural           
     Resources VRDO                          
     (Carnegie Hall)                         
     3.10%, 6/1/94                                600                            600
  New York Environmental                     
     Facilities PCR                          
     5.20%, 5/15/14                             1,500                          1,323
  New York State Dormitory Auth.             
     (City Univ.)                            
     10.00%, 7/1/95 (Prere.)                    5,570                          6,033
     (Columbia Univ.)                        
     4.75%, 7/1/12                              4,000                          3,394
     5.75%, 7/1/15                             11,965                         11,540
  New York State Energy Research             
     & Development Auth. PCR                 
     (New York State Electric & Gas)         
     2.80%, 12/1/94                               500                            499
  New York State Power Auth.                 
     7.00%, 1/1/09                              6,000                          6,450
  Onondaga County Public                     
     Improvements                            
     5.875%, 2/15/06                            1,580                          1,610
     5.875%, 2/15/08                            2,475                          2,504
</TABLE>


                                       8
<PAGE>   9
<TABLE>
<CAPTION>
                                                 Face                         Market
                                               Amount                          Value
                                                (000)                         (000)+
- - ------------------------------------------------------------------------------------
<S>                                           <C>                           <C>
  Port Auth. of New York &                   
     New Jersey Rev. VRDO                    
     3.00%, 6/1/94                            $ 6,500                       $  6,500
  Triborough Bridge & Tunnel Auth.           
     TOB VRDO 2.9%, 7/1/94                      3,200                          3,200
     7.00%, 7/1/95 (Prere.)                     2,000                          2,065
     6.00%, 1/1/12                              7,805                          7,796
  Westchester County GO                      
     6.70%, 11/1/08                             3,250                          3,573
     6.70%, 11/1/09                             3,645                          3,980
OUTSIDE NEW YORK:                            
  Puerto Rico Govt.                          
     Development Bank VRDO                   
     2.60%, 6/1/94                              2,600                          2,600
                                                                            --------
           GROUP TOTAL                                                        66,189
                                                                            --------
- - ------------------------------------------------------------------------------------
TOTAL MUNICIPAL BONDS (Cost $728,216)                                        741,991
- - ------------------------------------------------------------------------------------
OTHER ASSETS AND LIABILITIES (2.3%)          
- - ------------------------------------------------------------------------------------
     Other Assets--Note B                                                     19,525
     Liabilities                                                              (1,771)
                                                                            --------
                                                                              17,754
- - ------------------------------------------------------------------------------------
NET ASSETS (100%)                            
- - ------------------------------------------------------------------------------------
  Applicable to 72,435,647 outstanding       
     shares of beneficial interest           
     (unlimited authorization--no par value)                                $759,745
- - ------------------------------------------------------------------------------------
NET ASSET VALUE PER SHARE                                                     $10.49
====================================================================================
</TABLE>

+ See Note A to Financial Statements.

<TABLE>
<CAPTION>
- - ------------------------------------------------------------------------------------
AT MAY 31, 1994, NET ASSETS CONSISTED OF:    
- - ------------------------------------------------------------------------------------
                                               Amount                            Per
                                                (000)                          Share
                                             --------                         ------
  <S>                                        <C>                              <C>
  Paid in Capital                            $734,212                         $10.14
  Undistributed Net Investment Income              --                             --
  Accumulated Net Realized Gains                7,136                            .10
  Unrealized Appreciation of Investments--   
    Note D                                     18,397                            .25
- - ------------------------------------------------------------------------------------
  NET ASSETS                                 $759,745                         $10.49
- - ------------------------------------------------------------------------------------
</TABLE>

(1) MBIA (Municipal Bond Insurance Association)
(2) AMBAC (AMBAC Indemnity Corporation)
(3) FGIC (Financial Guaranty Insurance Company)
(4) FSA (Financial Security Assurance)
(5) CGI (Capital Guaranty Insurance)
(6) BIGI (Bond Investors Guaranty Insurance)
(7) Connie Lee Inc.
(8) FHA (Federal Housing Authority)
BAN--Bond Anticipation Note
COP--Certificate of Participation
CP--Commercial Paper
GO--General Obligation
IDR--Industrial Development Revenue
PCR--Pollution Control Revenue
RAN--Revenue Anticipation Note
TAN--Tax Anticipation Note
TOB--Tender Option Bond
TRAN--Tax Revenue Anticipation Note
VRDO--Variable Rate Demand Obligation
(ETM)--Escrowed to Maturity
(Prere.)--Prerefunded
*Put Option Obligation.

                                       9
<PAGE>   10
STATEMENT OF OPERATIONS

<TABLE>
<CAPTION>
                                                                                                         Six Months Ended
                                                                                                             May 31, 1994
                                                                                                                    (000)
- - -------------------------------------------------------------------------------------------------------------------------
<S>                                                                                   <C>                        <C>
INVESTMENT INCOME
  INCOME
- - -------------------------------------------------------------------------------------------------------------------------
    Interest  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                                   $22,580
- - -------------------------------------------------------------------------------------------------------------------------
          Total Income  . . . . . . . . . . . . . . . . . . . . . . . . . . . .                                    22,580
- - -------------------------------------------------------------------------------------------------------------------------
  EXPENSES
    The Vanguard Group--Note b
      Investment Advisory Services  . . . . . . . . . . . . . . . . . . . . . .       $  43
      Management and Administrative . . . . . . . . . . . . . . . . . . . . . .         703
      Marketing and Distribution  . . . . . . . . . . . . . . . . . . . . . . .          95                           841
                                                                                      -----                              
    Insurance Expense . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                                        13
    Auditing Fees . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                                         4
    Shareholders' Reports . . . . . . . . . . . . . . . . . . . . . . . . . . .                                        20
    Annual Meeting and Proxy Costs  . . . . . . . . . . . . . . . . . . . . . .                                         3
    Trustees' Fees and Expenses . . . . . . . . . . . . . . . . . . . . . . . .                                         2
- - -------------------------------------------------------------------------------------------------------------------------
          Total Expenses  . . . . . . . . . . . . . . . . . . . . . . . . . . .                                       883
- - -------------------------------------------------------------------------------------------------------------------------
            Net Investment Income . . . . . . . . . . . . . . . . . . . . . . .                                    21,697
- - -------------------------------------------------------------------------------------------------------------------------
REALIZED NET GAIN
    Investment Securities Sold  . . . . . . . . . . . . . . . . . . . . . . . .                                     4,500
    Futures Contracts . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                                     3,131
- - -------------------------------------------------------------------------------------------------------------------------
            Realized Net Gain . . . . . . . . . . . . . . . . . . . . . . . . .                                     7,631
- - -------------------------------------------------------------------------------------------------------------------------
CHANGE IN UNREALIZED APPRECIATION
  (DEPRECIATION)
    Investment Securities . . . . . . . . . . . . . . . . . . . . . . . . . . .                                   (47,398)
    Futures Contracts . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                                     4,337
- - -------------------------------------------------------------------------------------------------------------------------
            Change in Unrealized Appreciation (Depreciation)  . . . . . . . . .                                   (43,061)
- - -------------------------------------------------------------------------------------------------------------------------
            Net Decrease in Net Assets Resulting from Operations  . . . . . . .                                  $(13,733)
=========================================================================================================================
</TABLE>

                                       10
<PAGE>   11
STATEMENT OF CHANGES IN NET ASSETS

<TABLE>
<CAPTION>
                                                                           SIX MONTHS ENDED                    Year Ended
                                                                               MAY 31, 1994             November 30, 1993
                                                                                      (000)                         (000)
- - -------------------------------------------------------------------------------------------------------------------------
<S>                                                                               <C>                           <C>
INCREASE (DECREASE) IN NET ASSETS
OPERATIONS
  Net Investment Income . . . . . . . . . . . . . . . . . . . . . . .             $  21,697                     $  39,451
  Realized Net Gain . . . . . . . . . . . . . . . . . . . . . . . . .                 7,631                         1,421
  Change in Unrealized Appreciation (Depreciation)  . . . . . . . . .               (43,061)                       38,487
- - -------------------------------------------------------------------------------------------------------------------------
            Net Increase (Decrease) in Net Assets Resulting
            from Operations . . . . . . . . . . . . . . . . . . . . .               (13,733)                       79,359
- - -------------------------------------------------------------------------------------------------------------------------
DISTRIBUTIONS (1)
  Net Investment Income . . . . . . . . . . . . . . . . . . . . . . .               (21,697)                      (39,451)
  Realized Net Gain . . . . . . . . . . . . . . . . . . . . . . . . .                  (856)                       (8,055)
- - -------------------------------------------------------------------------------------------------------------------------
            Total Distributions . . . . . . . . . . . . . . . . . . .               (22,553)                      (47,506)
- - -------------------------------------------------------------------------------------------------------------------------
CAPITAL SHARE TRANSACTIONS (2)
  Issued       -- Regular . . . . . . . . . . . . . . . . . . . . . .                84,396                       270,638
               -- In Lieu of Cash Distributions . . . . . . . . . . .                17,008                        36,903
               -- Exchange  . . . . . . . . . . . . . . . . . . . . .                27,705                        65,532
  Redeemed     -- Regular . . . . . . . . . . . . . . . . . . . . . .               (74,466)                      (96,649)
               -- Exchange  . . . . . . . . . . . . . . . . . . . . .               (65,979)                      (74,611)
- - -------------------------------------------------------------------------------------------------------------------------
            Net Increase (Decrease) from Capital Share Transactions .               (11,336)                      201,813
- - -------------------------------------------------------------------------------------------------------------------------
            Total Increase (Decrease)   . . . . . . . . . . . . . . .               (47,622)                      233,666
- - -------------------------------------------------------------------------------------------------------------------------
NET ASSETS
  Beginning of Period . . . . . . . . . . . . . . . . . . . . . . . .               807,367                       573,701
- - -------------------------------------------------------------------------------------------------------------------------
  End of Period . . . . . . . . . . . . . . . . . . . . . . . . . . .              $759,745                      $807,367
=========================================================================================================================
  (1)       Distributions Per Share Net Investment Income . . . . . .                 $.294                         $.594
            Realized Net Gain . . . . . . . . . . . . . . . . . . . .                 $.012                         $.145
- - -------------------------------------------------------------------------------------------------------------------------
  (2)       Shares Issued and Redeemed Issued . . . . . . . . . . . .                10,366                        31,063
            Issued in Lieu of Cash Distributions  . . . . . . . . . .                 1,583                         3,424
            Redeemed  . . . . . . . . . . . . . . . . . . . . . . . .               (13,125)                      (15,771)
- - -------------------------------------------------------------------------------------------------------------------------
                                                                                     (1,176)                       18,716
- - -------------------------------------------------------------------------------------------------------------------------
</TABLE>


                                       11
<PAGE>   12
FINANCIAL HIGHLIGHTS

<TABLE>
<CAPTION>                                                                              Year Ended November 30,
                                                       SIX MONTHS ENDED    ----------------------------------------------
For a Share Outstanding Throughout Each Period             MAY 31, 1994      1993      1992      1991     1990       1989
- - -------------------------------------------------------------------------------------------------------------------------
<S>                                                              <C>      <C>       <C>       <C>        <C>      <C>
NET ASSET VALUE, BEGINNING OF PERIOD  . . . . . . . . . . .      $10.97    $10.45    $10.04     $9.66     $9.73     $9.26
INVESTMENT OPERATIONS
      Net Investment Income   . . . . . . . . . . . . . . .        .294      .594      .631      .639      .629      .635
      Net Realized and Unrealized Gain
        (Loss) on Investments   . . . . . . . . . . . . . .       (.468)     .665      .410      .380     (.070)     .470
                                                                 ------    ------    ------    ------    ------    ------
        TOTAL FROM INVESTMENT OPERATIONS    . . . . . . . .       (.174)    1.259     1.041     1.019      .559     1.105
- - -------------------------------------------------------------------------------------------------------------------------
DISTRIBUTIONS
      Dividends from Net Investment Income    . . . . . . .       (.294)    (.594)    (.631)    (.639)    (.629)    (.635)
      Distributions from Realized Capital Gains . . . . . .       (.012)    (.145)       --        --        --        --
                                                                 ------    ------    ------    ------    ------    ------
        TOTAL DISTRIBUTIONS   . . . . . . . . . . . . . . .       (.306)    (.739)    (.631)    (.639)    (.629)    (.635)
- - -------------------------------------------------------------------------------------------------------------------------
NET ASSET VALUE, END OF PERIOD    . . . . . . . . . . . . .      $10.49    $10.97    $10.45    $10.04     $9.66     $9.73
=========================================================================================================================
TOTAL RETURN    . . . . . . . . . . . . . . . . . . . . . .      -1.62%   +12.42%   +10.63%   +10.87%    +5.99%   +12.25%
- - -------------------------------------------------------------------------------------------------------------------------
RATIOS/SUPPLEMENTAL DATA
- - ------------------------
Net Assets, End of Period (Millions)  . . . . . . . . . . .        $760      $807      $574      $408      $241      $167
Ratio of Expenses to Average Net Assets . . . . . . . . . .       .22%*      .19%     .23%+     .27%+     .31%+     .34%+
Ratio of Net Investment Income to Average Net Assets  . . .      5.48%*     5.47%     6.11%     6.48%     6.60%     6.64%
Portfolio Turnover Rate . . . . . . . . . . . . . . . . . .        20%*       10%       28%       19%       17%       10%
- - -------------------------------------------------------------------------------------------------------------------------
</TABLE>

+Insurance expenses represent .01%, .01%, .02%, and .04%.
*Annualized.


                                       12
<PAGE>   13
NOTES TO FINANCIAL STATEMENTS

Vanguard New York Insured Tax-Free Fund is registered under the Investment
Company Act of 1940 as an open-end investment company.  The Fund invests in
securities of municipal issuers whose ability to meet their obligations may be
affected by economic and political developments in the State of New York.

* A. The following significant accounting policies are in conformity with
generally accepted accounting principles for investment companies. Such
policies are consistently followed by the Fund in the preparation of financial
statements.

1.   SECURITY VALUATION: Municipal bonds are valued utilizing primarily the
latest bid prices or, if bid prices are not available, on the basis of
valuations based on a matrix system (which considers such factors as
security prices, yields, maturities, and ratings), both as furnished by an
independent pricing service.

2.   FEDERAL INCOME TAXES: The Fund intends to continue to qualify as a
regulated investment company and distribute all of its income.
Accordingly, no provision for Federal income taxes is required in the
financial statements.

3.   FUTURES: The Fund utilizes futures contracts to a limited extent. The
primary risks associated with the use of futures contracts are imperfect
correlation between the change in market value of the bonds held by the
Fund and the prices of futures contracts, and the possibility of an
illiquid market. Futures contracts are valued based upon their quoted
daily settlement prices. Fluctuations in the value of futures contracts
are recorded as unrealized appreciation (depreciation) until terminated at
which time realized gains (losses) are recognized. Unrealized appreciation
(depreciation) related to open futures contracts is required to be treated
as realized gain (loss) for Federal income tax purposes.

4.   DISTRIBUTIONS: Distributions from net investment income are declared on a
daily basis payable on the first business day of the following month.
Annual distributions from realized gains, if any, are recorded on the
ex-dividend date.   Capital gain distributions are determined on a tax
basis and may differ from realized capital gains for financial reporting
purposes due to differences in the timing of realization of gains.

5.   OTHER: Security transactions are accounted for on the date the securities
are purchased or sold. Costs used in determining realized gains and losses
on the sale of investment securities are those of specific securities
sold. Premiums and original issue discounts are amortized and accreted,
respectively, to interest income over the lives of the respective
securities.

* B. The Vanguard Group, Inc. furnishes at cost investment advisory, corporate
management, administrative, marketing, and distribution services. The costs of
such services are allocated to the Fund under methods approved by the Board of
Trustees. The Fund has contributed capital of $120,000 to Vanguard (included in
Other Assets), representing .6% of Vanguard's capitalization. The Fund's
officers and trustees are also officers and directors of Vanguard.

* C. During the six months ended May 31, 1994, the Fund made purchases of
$75,750,000 and sales of $73,932,000 of investment securities other than
temporary cash investments.


                                       13
<PAGE>   14
NOTES TO FINANCIAL STATEMENTS (continued)

* D. At May 31, 1994, unrealized appreciation of investment securities for
financial reporting and Federal income tax purposes aggregated $13,775,000 of
which $25,556,000 related to appreciated securities and $11,781,000 related to
depreciated securities.

At May 31, 1994, the Fund had long positions in Municipal Bond Index futures
contracts expiring in June 1994, with an aggregate settlement value and net
unrealized appreciation of $19,659,000 and $106,000, respectively. The
aggregate settlement value and net unrealized appreciation related to short
positions in U.S. Treasury Bond futures contracts expiring through September
1994, were $89,164,000 and $4,516,000, respectively.  The market value of
securities deposited as initial margin for open futures contracts was
$2,029,000.



                                       14
<PAGE>   15
TRUSTEES AND OFFICERS


JOHN C. BOGLE, Chairman and Chief Executive Officer
Chairman and Director of The Vanguard Group, Inc., and of each of the
investment companies in The Vanguard Group.

JOHN J. BRENNAN, President
President and Director of The Vanguard Group, Inc., and of each of the
investment companies in The Vanguard Group.

ROBERT E. CAWTHORN, Chairman and Chief Executive Officer of Rhone-Poulenc Rorer
Inc.; Director of Sun Company, Inc. and Immune Response Corporation; Trustee of
the Universal Health Realty Income Trust.

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

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

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

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

JAMES O. WELCH, JR., Retired Chairman of Nabisco Brands, Inc.; retired Vice
Chairman and Director of RJR Nabisco; Director of TECO Energy, Inc.

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


OTHER FUND OFFICERS

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

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.

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

OTHER VANGUARD GROUP OFFICERS

JEREMY G. DUFFIELD
Senior Vice President
Planning & Development

JAMES H. GATELY
Senior Vice President
Institutional

IAN A. MACKINNON
Senior Vice President
Fixed Income Group

VINCENT S. MCCORMACK
Senior Vice President
Operations

RALPH K. PACKARD
Senior Vice President
Chief Financial Officer

                                       15
<PAGE>   16
                          THE VANGUARD FAMILY OF FUNDS

                               MONEY MARKET FUNDS
                         Vanguard Money Market Reserves

                         TAX-EXEMPT MONEY MARKET FUNDS
              Vanguard Municipal Bond Fund-Money Market Portfolio
                 Vanguard State Tax-Free Funds (CA, NJ, OH, PA)

                            TAX-EXEMPT INCOME FUNDS
                          Vanguard Municipal Bond Fund
             Vanguard State Tax-Free Funds (CA, FL, NJ, NY, OH, PA)

                               FIXED INCOME FUNDS
                             Vanguard Admiral Funds
                            Vanguard Bond Index Fund
                     Vanguard Fixed Income Securities Fund
                         Vanguard Preferred Stock Fund

                                 BALANCED FUNDS
                         Vanguard Asset Allocation Fund
                          Vanguard Balanced Index Fund
                               Vanguard STAR Fund
                         Vanguard/Wellesley Income Fund
                            Vanguard/Wellington Fund

                                  EQUITY FUNDS
                            GROWTH AND INCOME FUNDS
                      Vanguard Convertible Securities Fund
                          Vanguard Equity Income Fund
                              Vanguard Index Trust
                        Vanguard Quantitative Portfolios
                 Vanguard/Trustees' Equity Fund-U.S. Portfolio
                             Vanguard/Windsor Fund
                              Vanguard/Windsor II

                                  GROWTH FUNDS
                          Vanguard/Morgan Growth Fund
                             Vanguard/PRIMECAP Fund
                         Vanguard U.S. Growth Portfolio

                            AGGRESSIVE GROWTH FUNDS
                             Vanguard Explorer Fund
                        Vanguard Specialized Portfolios

                              INTERNATIONAL FUNDS
                    Vanguard International Equity Index Fund
                    Vanguard International Growth Portfolio
             Vanguard/Trustees' Equity Fund-International Portfolio


                 The Vanguard Group * Vanguard Financial Center
                             Valley Forge, PA 19482
                   New Account Information: 1-(800) 662-7447
                 Shareholder Account Services: 1-(800) 662-2739
               This Report has been prepared for shareholders and
                may be distributed to others only if preceded or
             accompanied by a current prospectus. All Funds in the
                Vanguard Family are offered by prospectus only.

                                  Q762-05/94

                                   VANGUARD
                               NEW YORK INSURED
                                TAX FREE FUND
                                      
                        [PHOTO -- SEE EDGAR APPENDIX]

                              SEMI-ANNUAL REPORT
                              MAY 31, 1994
<PAGE>   17
                                 EDGAR APPENDIX

     The back cover of the printed version of this report features the flags of
the United States of America and Vanguard flying from a halyard.


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