SecProbe.io

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                P.O. Box 2600

                Valley Forge, PA 19482-2600

                610-669-9296

                anthony_coletta@vanguard.com

    November 4, 2021

    Lisa N. Larkin, Esq.

    Chad Eskildsen

    U.S. Securities and Exchange Commission
              via
        electronic filing

    100 F Street, N.E.

    Washington, DC 20549

               RE:

              Vanguard Chester Funds (the “Registrant”)

              File Nos. 333-260047; 333-260048; 333-260049; 333-260050; 333-260051; 333-260052; 333-260053; 333-260054; 333-260055; 333-260056; 333-260057; 333-260058

              Registration Statements on Form N-14

      Dear Ms. Larkin and Mr. Eskildsen:

      This letter responds to the comments you provided on October 25, 2021 and November 2, 2021, to the Registrant’s Registration Statements on Form N-14 (the
        “Registration Statements”) filed with the Commission on October 5, 2021, in connection with the following reorganizations:

              Acquired Funds (each, an “Acquired Fund” and collectively, the “Acquired Funds”)

              Acquiring Funds (each, an “Acquiring Fund”; collectively, the “Acquiring Funds”; and together with the Acquired Funds, the
                “Funds”)

              Vanguard Institutional Target Retirement Income Fund

              Vanguard Target Retirement Income Fund

              Vanguard Institutional Target Retirement 2015 Fund

              Vanguard Target Retirement 2015 Fund

              Vanguard Institutional Target Retirement 2020 Fund

              Vanguard Target Retirement 2020 Fund

              Vanguard Institutional Target Retirement 2025 Fund

              Vanguard Target Retirement 2025 Fund

              Vanguard Institutional Target Retirement 2030 Fund

              Vanguard Target Retirement 2030 Fund

              Vanguard Institutional Target Retirement 2035 Fund

              Vanguard Target Retirement 2035 Fund

              Vanguard Institutional Target Retirement 2040 Fund

              Vanguard Target Retirement 2040 Fund

              Vanguard Institutional Target Retirement 2045 Fund

              Vanguard Target Retirement 2045 Fund

              Vanguard Institutional Target Retirement 2050 Fund

              Vanguard Target Retirement 2050 Fund

              Vanguard Institutional Target Retirement 2055 Fund

              Vanguard Target Retirement 2055 Fund

              Vanguard Institutional Target Retirement 2060 Fund

              Vanguard Target Retirement 2060 Fund

              Vanguard Institutional Target Retirement 2065 Fund

              Vanguard Target Retirement 2065 Fund

      The Acquired Funds and the Acquiring Funds are each a series of the Registrant. Capitalized terms used herein, and not otherwise defined, have the meanings
        assigned in the Registration Statements. Responses apply to all Funds, as applicable, unless otherwise noted.

            Lisa N. Larkin, Esq.

            November 4, 2021

            Page 2

              Comment 1:

              Key Points About the Reorganization

              Comment:

              In the “Lower Costs for Shareholders” section, please clarify how the Combined Fund will achieve the reduced expense ratio.

              Response:

              The Registrant has revised the disclosure to clarify that the Combined Fund will achieve the reduced expense ratio by investing in lower-cost share
                classes of the underlying funds.

              Comment 2:

              Comparison of Principal Investment Strategies

              Comment:

              In the “Comparison of Principal Investment Strategies” section, please clarify that information about the Funds’ asset allocation strategies is
                available in the Prospectus.

              Response:

              The Registrant has revised the disclosure in the manner requested.

              Comment 3:

              Comparison of Fees and Expenses

              Comment:

              Please confirm that there have not been any material changes to the fees and expenses provided as of March 31, 2021.

              Response:

              The Registrant confirms that there have not been any material changes to the fees and expenses provided as of March 31, 2021.

              Comment 4:

              Comparison of Fees and Expenses

              Comment:

              Please supplementally explain why Acquired Fund Fees and Expenses are being restated.

              Response:

              Each Fund’s expense ratio is based solely on the fees and expenses associated with the Fund’s investments in the underlying funds. Each Combined
                Fund is expected to have an expense ratio of 8 basis points, which is lower than the current expense ratios for each Acquiring Fund and Acquired Fund. To achieve the lower expense ratio, each Combined Fund will reduce its Acquired Fund Fees
                and Expenses by investing in lower-cost share classes of the underlying funds. Accordingly, the Registrant has restated Acquired Fund Fees and Expenses and Total Annual Fund Operating Expenses to reflect expenses anticipated at the time of
                the closing of the Reorganizations.

              Comment 5:

              Comparison of Portfolio Turnover

              Comment:

              Please confirm that each Fund’s portfolio turnover rate will be completed in the definitive filing.

              Response:

              The Registrant confirms that each Fund’s portfolio turnover rate, as well as any other outstanding information, will be completed in the definitive
                filing.

            Lisa N. Larkin, Esq.

            November 4, 2021

            Page 3

              Comment 6:

              Asset Allocation Framework

              Comment:

              In the “Asset Allocation Framework” section, please update the targeted asset allocation table with more recent information or, in the alternative,
                confirm that more recent information is not available.

              Response:

              The Registrant has updated the targeted asset allocation table with information as of September 30, 2021.

              Comment 7:

              Asset Allocation Framework

              Comment:

              Consider revising the format of the asset allocation framework tables.

              Response:

              The Registrant respectfully declines to make this change. The presentation of the asset allocation framework tables is consistent with the
                presentation in the Funds’ prospectuses and the Registrant believes that it facilitates a shareholder’s ability to review the targeted asset allocation for the Acquiring and Acquired Funds.

              Comment 8:

              Asset Allocation Framework (Vanguard Institutional Target Retirement 2015 Fund and Vanguard Target Retirement 2015 Fund)

              Comment:

              Please supplementally confirm when Vanguard Institutional Target Retirement 2015 Fund and Vanguard Target Retirement 2015 Fund will be combined with
                the Target Retirement Income Fund.

              Response:

              As described in the Vanguard Institutional Target Retirement 2015 Fund prospectus and the Vanguard Target Retirement 2015 Fund prospectus, once the
                Fund’s asset allocation is similar to that of the Target Retirement Income Fund, the Fund’s board of trustees may approve combining the Fund with the Target Retirement Income Fund. The Registrant expects the combination to occur within
                seven years after 2015 and sometime following the closing of the merger of Vanguard Institutional Target Retirement 2015 Fund with and into Vanguard Target Retirement 2015 Fund.

              Comment 9:

              Information About the Reorganization

              Comment:

              In the “Information About the Reorganization” section, please revise the disclosure to clarify when the Acquired Fund will be closed to investments.

              Response:

              The Registrant has revised the disclosure to clarify that approximately two business days before the Reorganization is scheduled to occur, the
                Acquired Fund will be closed for any investment.

              Comment 10:

              Capitalization Table

              Comment:

              Please update the capitalization table to reflect data from within 30 days of the filing of each Registration Statement.

              Response:

              The Registrant has revised the disclosure in the manner requested.

            Lisa N. Larkin, Esq.

            November 4, 2021

            Page 4

              Comment 11:

              Appendix B

              Comment:

              Please supplementally confirm that the Summary Prospectus will be included with the definitive filing.

              Response:

              The Registrant confirms that the Summary Prospectus will be included with the definitive filing.

              Comment 12:

              Tax Opinion

              Comment:

              Please supplementally confirm the manner in which the final Tax Opinions will be filed.

              Response:

              The Registrant intends to file the final Tax Opinions in a post-effective amendment following the closing of the Reorganizations.

      Please contact me at 610-669-9296 or anthony_coletta@vanguard.com with
        any questions or concerns regarding the above.

      Sincerely,

      /s/ Anthony Coletta

      Anthony V. Coletta, Jr.

      Senior Counsel

      The Vanguard Group, Inc.