{SHIP GRAPHIC}VANGUARD(R)



                                                     January 26, 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 (the "Trust")

Dear Mr. Sandoe:

         The following responds to your comments of January 12, 2006 on the
post-effective amendment of the registration statement of the above-referenced
registrant. You commented on Post-Effective Amendment No. 33 that was filed on
November 29, 2005.


Comment 1:  Vanguard PRIMECAP Fund Prospectus:  Performance/Risk Information

Comment:          Should the following sentence be removed from page 1 of the
                  prospectus since it does not apply to the Vanguard PRIMECAP
                  Fund? "If applicable shareholder fees were reflected, returns
                  would be less than those shown."

Response:         The sentence has been removed since it does not apply to the
Fund.


Comment 2:        Vanguard Target Retirement Funds Prospectus: Risk Disclosure

Comment:          On page 5 the prospectus states that the 2005 Target
                  Retirement Fund's indirect stock holdings consist
                  substantially of large-capitalization U.S. stocks and, to a
                  lesser extent, of mid-and small-cap U.S. stocks.  Please add
                  mid-cap risk as a primary investment risk of the Fund.

Response:         We believe the disclosure is appropriate as written. The 2005
                  Fund invests in four underlying Vanguard funds, one of
                  which is the Vanguard Total Stock Market Index Fund.  The
                  Total Stock Market Index Fund seeks to track the performance
                  of the MSCI US Broad Market Index by investing primarily in
                  the largest stocks in the Index. Since the MSCI US Broad
                  Market Index, with a median market-cap of approximately $27
                  billion, is dominated by large-cap stocks, we do not consider
                  the much lesser existence of the mid- and small-cap stocks, to
                  warrant inclusion of this

January 26, 2006
Christian Sandoe
Page 2 of 4



                  disclosure in the primary investment strategies and risks
                  section.  This is especially true in light of the fact that
                  equity securities only account for approximately 30% of the
                  Fund's total assets.  We discuss the risks of mid- and small-
                  cap stocks in the Item 4 disclosure and we are comfortable
                  with that disclosure in that location.

Comment 3:        Vanguard Target Retirement Funds Prospectus: Fundamental
                  Objective

Comment:          Is each Target Retirement Fund's objective fundamental?

Response:         Each Target Retirement Fund's objective is fundamental, and is
                  disclosed as such in the Fund's Statement of Additional
                  Information.  No additional Prospectus disclosure is required.

Comment 4:        Vanguard Target Retirement Funds Prospectus: Diversification.

Comment:          On page 22, modify the final sentence in the paragraph "More
                  on the Funds," to clarify that these funds, while classified
                  as nondiversified, have actually "operated as" diversified.

Response:         We believe the current disclosure is appropriate. The Target
                  Retirement Funds are "funds of funds," that hold only four or
                  five underlying Vanguard mutual funds. For this reason they
                  are nondiversified. However, each fund indirectly owns a
                  diversified portfolio of stocks and bonds. Moreover, each of
                  the Target Retirement Funds is registered as a nondiversified,
                  open-end, management investment company.

Comment 5:        Statement of Additional Information: Portfolio Manager
                  Disclosure.

Comment:          On page B-36, please clarify the accounts that are jointly and
                  separately managed by the PRIMECAP portfolio managers.

Response:         We have identified accounts that are jointly managed by the
                  PRIMECAP managers, and accounts that are separately managed.

Comment 6:        Statement of Additional Information: Portfolio Manager
                  Disclosure.

Comment:          On page B-36, please clarify what the material conflicts of
                  interest are, and how PRIMECAP will respond to them.

Response:         We believe the disclosure adequately identifies the material
                  conflicts by stating: "potential conflicts of interest . . .
                  may arise between mutual funds and separate accounts, whereby
                  a client or clients may be disadvantaged by trades executed in
                  other clients' portfolios on the same security." PRIMECAP
                  manages these risks, as noted in the disclosure, by adopting
                  best execution and trade allocation policies and procedures to
                  prevent conflicts between mutual funds and separate accounts.
                  In addition, such


January 26, 2006
Christian Sandoe
Page 3 of 4

                  policies and procedures are strictly monitored and are
                  reviewed continuously by PRIMECAP.

Comment 7:        Statement of Additional Information: Portfolio Manager
                  Disclosure.

Comment:          On page B-37, please identify whether the portfolio manager's
                  base compensation is fixed.

Response:         The modified disclosure on portfolio manager compensation
                  notes that "[e]ach portfolio manager receives a fixed salary
                  that is in part based on industry experience, as well as
                  contribution to the firm." The disclosure also includes a
                  description of bonus structure and profit sharing
                  arrangements.

Comment 8:        Statement of Additional Information: Portfolio Manager
                  Disclosure.

Comment:          On page B-38, please identify the benchmark indexes from which
                  portfolio managers are paid.

Response:         The disclosure notes that a portfolio manager's performance is
                  tracked against the fund's benchmark index over a one-year
                  period.  Each fund's benchmark is identified in that fund's
                  prospectus.

Comment 9:        Statement of Additional Information: Power of Attorney.

Comment:          Please modify your Power of Attorney to clarify the registrant
                  numbers for each Vanguard registrant.

Response:         A Power of Attorney will be filed that details each Vanguard
                  registrant's Securities Act of 1933 filing number.

Comment 10:       Tandy Requirements

Comment:          The SEC is now requiring all registrants to provide at the end
                  of response letters to registration statement comments, the
                  following statements:

                  - The Trust 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 Trust 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.

Response:         As required by the SEC, we will provide the foregoing
                  acknowledgements.

                                        * * * * *

                                       2

January 26, 2006
Christian Sandoe
Page 4 of 4


              As required by the SEC, the Trust acknowledges that:

              - The Trust 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 Trust 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) 669-5284 with any questions or comments
regarding the above responses. Thank you.

                                                     Sincerely,

                                                     /s/ Lisa Matson
                                                     Lisa  Matson
                                                     Associate Counsel