[SHIP GRAPHIC] VANGUARD(R)

                                                    P.O. Box 2600
                                                    Valley Forge, PA 19482-2600

                                                    610-669-1538
                                                    Judy_L_Gaines@vanguard.com

May 9, 2006


Christian Sandoe, Esq.
Division of Investment Management
U.S. Securities and Exchange Commission                    via electronic filing
450 Fifth Street,
N.W., Fifth Floor
Washington, D.C. 20549

RE:      Vanguard Chester Funds


Dear Mr. Sandoe,

     The   following   responds  to  your   comments  of  May  8,  2006  on  the
post-effective  amendment of the registration  statement of the above-referenced
registrant.  You commented on Post-Effective  Amendment No. 35 that was filed on
March 20, 2006.


Comment 1:        PROSPECTUS - PRIMARY INVESTMENT STRATEGIES - EACH FUND

Comment:          The disclosure states that each Fund's indirect stock holdings
                  consist substantially of large-cap U.S. stocks and, to a
                  lesser extent, of mid- and small- cap U.S. stocks.  If the
                  presence of mid- and small-cap stocks is significant
                  enough to warrant it, there should be corresponding primary
                  risk disclosure.

Response:         Vanguard Total Stock Market Index Fund invests across all
                  market-capitalization segments, and does not focus on a
                  particular category of stocks. Based on the small percentage
                  of this fund that is invested in small- and mid-cap stocks,
                  and the fact that only a portion of each fund's assets are
                  invested in this fund, we do not believe it is appropriate to
                  add mid- or small-cap risk as a primary risk of the Funds.

Comment 2:        PROSPECTUS - PRIMARY RISKS - EACH FUND

Comment:          Certain Funds include Manager Risk as a primary risk while
                  others do not. Please explain the basis for the inconsistency.

Response:         To the extent that a Fund invests in solely in index funds, we
                  do not consider Manager Risk to be a primary risk of the Fund.
                  However, to the extent that a Fund invests in actively managed
                  funds to a significant extent, we do consider Manager Risk to
                  be a primary risk. We have included Manager Risk as a primary
                  risk in some Fund profiles and not others based on this
                  analysis of each Fund's underlying fund investments.


Christian Sandoe, Esq.
May 9, 2006
Page 2
                  Accordingly, we will amend the sentence to read, "Please refer
                  to the Performance of a Different but Similar Investment
                  Vehicle section of this prospectus for information on the
                  performance of a different but similar investment vehicle."

Comment 3:        PROSPECTUS - PERFORMANCE/RISK INFORMATION - 2015 FUND

Comment:          Under Comparative Indexes in the average annual total return
                  table, the Lehman Brothers Aggregate Bond Index appears first,
                  but bonds only comprise 33.3% of the Fund's holdings.

Response:         We will amend the order of the comparative indexes so the
                  equity indexes precede the bond index.

Comment 4:        PROSPECTUS - MORE ON THE FUNDS - EACH FUND

Comment:          Please explain why the Fund profiles do not include non-
                  diversification risk as a primary risk.

Response:         We do not consider non-diversification risk to be a primary
                  risk for the Funds. Each Fund, as a fund of funds, is
                  classified as non-diversified solely because of a position
                  taken by the Commission staff several years ago. In reality,
                  each Fund's portfolio is thoroughly diversified, and that is
                  unlikely to change in the foreseeable future. Accordingly,
                  highlighting non-diversification as a risk in Item 2, in our
                  view, would actually mislead investors about the risks of a
                  Fund. General Instruction C.1(b) of Form N-1A admonishes funds
                  not to "disproportionately emphasiz[e] possible investments or
                  activities of the Fund that are not a significant part of the
                  Fund's operations."(1)

                  The likelihood of a fund of funds ever being hurt
                  disproportionately by a decline in the prices of just a few
                  securities is extremely remote. All of Vanguard's
                  funds-of-funds, on a look-through basis, invest in hundreds of
                  securities and easily meet the diversification tests of the
                  Investment Company Act. Nevertheless, we will continue to
                  disclose, in Item 4, that the Fund is classified as
                  non-diversified and explain why that is.

Comment 5:        PROSPECTUS - ASSET ALLOCATION FRAMEWORK

Comment:          How can the Funds combine with the Target Retirement Fund
                  without shareholder approval?

Response:         The Trust's agreement and declaration of trust allows for this
                  type of merger upon the approval of the board of trustees. In
                  approving any such merger, the board would consider the
                  relevant factors and make the relevant findings as required by
                  Rule 17a-8 under the Investment Company Act of 1940.

Comment 6:        SAI - DATE OF PROSPECTUSES

Comment:          The SAI and Target Retirement Funds prospectus will be
                  effective as of June 2006, but the prospectus for PRIMECAP
                  Fund, another series of Vanguard Chester Funds, is dated
                  January

- ----------------------------------------------------
1 See also Investment Company Act Release No. 23064 (March 13, 1998) In adopting
Form N-1A, the Commission stated that the purpose of the summary risk disclosure
in a fund's prospectus is to identify briefly the principal risks of investing
in the particular fund and to emphasize those risks reasonable likely to affect
the fund's performance.


Christian Sandoe, Esq.
May 9, 2006
Page 3

                  2006. How can the January prospectus incorporate by
                  reference an SAI that did not exist until June?

Response:         In response to Item 1(b) of Form N-1A, we disclose on the back
                  cover of the PRIMECAP prospectus (and all other fund
                  prospectuses) that:

                  "The SAI contains more detailed information about the Fund.
                  The current annual and semiannual reports and the SAI are
                  incorporated by reference into (and are thus legally a part
                  of) this prospectus.

                  To receive a free copy of the latest annual or semiannual
                  report or the SAI, or to request additional information about
                  the Fund or other Vanguard funds, please visit our website or
                  contact us as follows."

                  Our use of the terms "current" and "latest" are intended to
                  make clear to investors that we are incorporating by reference
                  the most recent version of SAI.

Comment 7:        TANDY REQUIREMENTS

As required by the SEC, the Fund acknowledges that:

                  - The Fund is responsible for the adequacy and accuracy of the
                    disclosure in the filing.

                  - Staff comments or changes in response to staff comments in
                    the filings reviewed by the staff do not foreclose the
                    Commission from taking any action with respect to the
                    filing.

                  - The Fund may not assert staff comments as a defense in any
                    proceeding initiated by the Commission or any person under
                    the federal securities laws of the United States.

     Please  contact  me at  (610)  669-1538  with  any  questions  or  comments
regarding the above responses. Thank you.

Sincerely,


Judith L. Gaines
Associate Counsel
Securities Regulation, Legal Department