<PAGE>

     As filed with the Securities and Exchange Commission on June 21, 1999
                                                 Registration Statement No. 333-
================================================================================

                      SECURITIES AND EXCHANGE COMMISSION
                            Washington, D.C. 20549

                            _______________________

                                   FORM S-8
                            REGISTRATION STATEMENT
                                     UNDER
                          THE SECURITIES ACT OF 1933

                            _______________________

                            CHITTENDEN CORPORATION
            (Exact name of Registrant as Specified in Its Charter)

          Vermont                                           03-0228404
 (State of Incorporation)                     (I.R.S. Employer Identification #)

                             Two Burlington Square
                          Burlington, Vermont  05401
                                (802) 658-4000
      (Address, including zip code, and telephone number, including area
              code, of Registrant's principal executive offices)

 VERMONT FINANCIAL SERVICES CORP. AMENDED AND RESTATED 1994 STOCK OPTION PLAN
                    EASTERN BANCORP, INC. STOCK OPTION PLAN
                  VERMONT FEDERAL BANK, FSB STOCK OPTION PLAN
                 WEST MASS BANKSHARES, INC. STOCK OPTION PLAN
                           (Full Title of the Plan)

                            _______________________

                               Paul A. Perrault
                        Chairman, President and C.E.O.
                            Chittenden Corporation
                             Two Burlington Square
                          Burlington, Vermont  05401
                                (802) 658-4000
     (Name, address, including zip code, and telephone number, including
                       area code, of agent for service)


                                With copies to:
                           F. Sheldon Prentice, Esq.
             Senior Vice President, General Counsel and Secretary
                            Chittenden Corporation
                             Two Burlington Square
                          Burlington, Vermont  05401
                                (802) 658-4000

                            _______________________

                        CALCULATION OF REGISTRATION FEE
<TABLE>
<CAPTION>
========================================================================================================================
  Title of Securities         Amount to be           Proposed Maximum        Proposed Maximum             Amount of
   Being Registered          Registered (1)      Offering Price Per Share   Aggregate Offering Price   Registration Fee
------------------------------------------------------------------------------------------------------------------------
<S>                          <C>                 <C>                        <C>                        <C>
Common Stock, par value        464,456 (2)             $28.84375(6)                $14,515,012             $4,036(7)
 $1.00 per share                31,073 (3)
                                 6,630 (4)
                                 1,070 (5)
========================================================================================================================
</TABLE>

(1) Plus such additional number of shares as may be required in the event of a
    stock dividend, stock split, split-up, recapitalization or other similar
    event.

(2) This Registration Statement relates to 464,456 shares of Chittenden
    Corporation's ("Chittenden's") common stock that may be issued upon the
    exercise of options issued under the Vermont Financial Services Corp.
    Amended and Restated 1994 Stock Option Plan, which was assumed by Chittenden
    upon consummation of the merger of Vermont Financial Services Corp. with and
    into Chittenden, with Chittenden as the surviving corporation, on May 28,
    1999.

(3) This Registration Statement relates to 31,073 shares of Chittenden's common
    stock that may be issued upon the exercise of options issued under the
    Eastern Bancorp, Inc. Stock Option Plan, which was assumed by Chittenden
    upon consummation of the merger of Vermont Financial Services Corp. with and
    into Chittenden, with Chittenden as the surviving corporation, on May 28,
    1999.

(4) This Registration Statement relates to 6,630 shares of Chittenden's common
    stock that may be issued upon the exercise of options issued under the
    Vermont Federal Bank, FSB Stock Option Plan, which was assumed by Chittenden
    upon consummation of the merger of Vermont Financial Services Corp. with and
    into Chittenden, with Chittenden as the surviving corporation, on May 28,
    1999.

(5) This Registration Statement relates to 1,070 shares of Chittenden's common
    stock that may be issued upon the exercise of options issued under the West
    Mass Bankshares, Inc. Stock Option Plan, which was assumed by Chittenden
    upon consummation of the merger of Vermont Financial Services Corp. with and
    into Chittenden, with Chittenden as the surviving corporation, on May 28,
    1999.

(6) This estimate is based on the average of the high and low sales prices on
    the New York Stock Exchange of the common stock of Chittenden on June 15,
    1999, pursuant to Rule 457(c) and (h) under the Securities Act of 1933, as
    amended, and is made solely for the purposes of determining the registration
    fee.

(7) In connection with the filing of its Registration Statement on Form S-4
    (File No. 333-75769), Chittenden paid a registration fee on an aggregate of
    15,496,225 shares of common stock, calculated in accordance with Rule
    457(f)(1), including 503,229 shares of Chittenden=s common stock issuable
    upon exercise of the options under the Vermont Financial Services Corp.
    Amended and Restated 1994 Stock Option Plan, Vermont Federal Bank, FSB Stock
    Option Plan, Eastern Bancorp, Inc. Stock Option Plan and West Mass
    Bankshares, Inc. Stock Option Plan.  Accordingly, pursuant to Rule 457(b),
    Chittenden is applying $4,036, the portion of the fee paid under the
    Form S-4 Registration Statement for the common stock issuable upon
    exercise of such options, against the fee payable for the securities
    registered hereunder.

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

<PAGE>

                                    PART II

              INFORMATION REQUIRED IN THE REGISTRATION STATEMENT


Item 3.   Incorporation of Certain Documents by Reference.
          -----------------------------------------------

     Chittenden Corporation ("Chittenden") hereby incorporates by reference the
following documents which have been previously filed with the Securities and
Exchange Commission (the "Commission"):

     (a)  The annual report filed on Form 10-K for the fiscal year ended
          December 31, 1998, filed with the Commission on March 24, 1999,
          pursuant to the Securities Exchange Act of 1934, as amended (the
          "Exchange Act");

     (b)  The Quarterly Report on Form 10-Q for the quarter ended March 31,
          1999, filed with the Commission on May 14, 1999, pursuant to the
          Exchange Act;

     (c)  The Current Report on Form 8-K/A filed on January 9, 1999, the Current
          Report on Form 8-K filed on May 6, 1999, and the Current Report on
          Form 8-K filed on June 11, 1999, all of which were filed with the
          Commission pursuant to the Exchange Act; and

     (d)  The description of Chittenden's Common Stock contained in its
          Registration Statement on Form 8-A, filed with the Commission on
          January 9, 1998, under Section 12 of the Exchange Act, and any
          amendments or reports filed for the purpose of updating such
          description.

     In addition, all documents subsequently filed with the Securities and
Exchange Commission by Chittenden pursuant to Sections 13(a), 13(c), 14 and
15(d) of the Exchange Act, prior to the filing of a post-effective amendment
which indicates that all securities offered hereunder have been sold or which
deregisters all securities then remaining unsold, shall be deemed to be
incorporated by reference in this Registration Statement and to be a part hereof
from the date of filing of such documents. Any statement contained in a document
incorporated or deemed to be incorporated by reference herein shall be deemed to
be modified or superseded for purposes hereof to the extent that a statement
contained herein or in any other subsequently filed document which also is
incorporated or deemed to be incorporated by reference herein modifies or
supersedes such statement. Any such statement so modified or superseded shall
not be deemed, except as so modified or superseded, to constitute a part of this
Registration Statement.

Item 4.   Description of Securities.
          -------------------------

     Not Applicable.

Item 5.   Interests of Named Experts and Counsel.
          --------------------------------------

     Certain legal matters in connection with the issuance of the Common Stock
offered by this Registration Statement are being passed upon for Chittenden by
F. Sheldon Prentice, Esq., Senior Vice President, General Counsel and Secretary
of Chittenden.

Item 6.   Indemnification of Directors and Officers.
          -----------------------------------------

     The Vermont Business Corporation Act ("VBCA") permits a corporation to
indemnify a director against judgements, penalties, fines, settlements and
reasonable expenses actually incurred by them in connection with any proceeding
to which they may be made a party by reason of their service in that capacity
if:  (1) the director conducted himself or herself in good faith, (2) the
director reasonably believed that his or her conduct, in an
<PAGE>

official capacity with the corporation, was in the best interests of the
corporation and, in all other cases, the conduct was at least not opposed to its
best interests, and (3) in a proceeding brought by a governmental entity, the
director had no reasonable cause to believe his or her conduct was unlawful, and
the director is not finally found to have engaged in a reckless or intentional
unlawful act. The termination of a proceeding by judgment, order, settlement,
conviction, or upon a plea of nolo contendre is not, of itself, determinative
that the director did not meet the standard of conduct necessary for
indemnification. Notwithstanding the foregoing, a corporation may not indemnify
a director if the director was adjudged liable: (a) to the corporation in a
proceeding by or in the right of a corporation, or (b) on the basis that a
personal benefit was improperly received by the director in a proceeding
charging improper personal benefit to the director. In addition, the VBCA
provides that, unless limited in a corporation's charter, a corporation shall
indemnify its directors and officers who are wholly successful, on the merits or
otherwise, in the defense of any proceeding to which the directors or officers
are parties by reason of their service in those capacities against reasonable
expenses incurred in connection with the proceeding. Chittenden's charter does
not limit such statutory right to indemnification.

     As permitted by the VBCA, Chittenden's bylaws provide that Chittenden shall
indemnify its directors and officers to the fullest extent provided by the
general laws of the State of Vermont, including the advancement of expenses
under the procedures provided by such laws. In addition, Chittenden's bylaws
contain the procedures pursuant to which such indemnification is effectuated.

     The VBCA permits the charter of a Vermont corporation to include a
provision eliminating or limiting the liability of a director to the corporation
or its stockholders for money damages for any action taken, or any failure to
take any action, solely as a director, based on a failure to discharge his or
her duties, except for (i) the amount of a financial benefit received by a
director to which the director is not entitled; (ii) an intentional or reckless
infliction of harm on the corporation or the stockholders; (iii) voting for or
assenting to an unlawful distribution or (iv) an intentional or reckless
criminal act. Chittenden's charter provides for the elimination of such
liability to the full extent provided by Vermont law.

     As permitted by the VBCA, Chittenden maintains directors and officers
liability insurance in amounts and on terms which the Chittenden Board of
Directors deems reasonable. In the ordinary course of business, the Chittenden
Board of Directors regularly reviews the scope and adequacy of such insurance
coverage.

Item 7.   Exemption from Registration Claimed.
          -----------------------------------

     Not Applicable.

Item 8.   Exhibits.
          --------

     (a)  The following is a complete list of exhibits filed or incorporated by
reference as part of this Registration Statement.

Exhibit
-------

    5.1   Opinion of F. Sheldon Prentice, as to the legality of the securities
          being registered.
    23.1  Consent of Arthur Andersen LLP.
    23.2  Consent of KMPG LLP.
    23.3  Consent of PricewaterhouseCoopers LLP.
    23.4  Consent of Counsel, F. Sheldon Prentice (included in Exhibit 5.1
          hereto).
    24.1  Power of Attorney (included on the signature page hereto).
    99.1  Vermont Financial Services Corp. Amended and Restated 1994 Stock
          Option Plan.  (Incorporated by reference to an attachment to the Proxy
          Statement filed by Vermont Financial Services Corp.

                                       2
<PAGE>

          on April 22, 1998).
    99.2  Eastern Bancorp, Inc. Stock Option Plan. (Incorporated by reference to
          Exhibit 4.1 of the Registration Statement filed by Vermont Financial
          Services Corp. on Form S-8 (File No. 333-30251) on June 27, 1997).
    99.3  Vermont Federal Bank, FSB Stock Option Plan. (Incorporated by
          reference to Exhibit 4.1 of the Registration Statement filed by
          Vermont Financial Services Corp. on Form S-8 (File No. 333-30251) on
          June 27, 1997).
    99.4  West Mass Bankshares, Inc. Stock Option Plan. (Incorporated by
          reference to Exhibit 4.1.(d) of the Registration Statement filed by
          Vermont Financial Services Corp. on Form S-8 (File No. 33-58259) on
          March 24, 1995).

Item 9.   Undertakings.
          ------------

     (a)  The undersigned Registrant hereby undertakes:

          (1)  To file, during any period in which offers or sales are being
               made, a post-effective amendment to this registration statement:

               (i)   To include any prospectus required by Section 10(a)(3) of
                     the Securities Act;

               (ii)  To reflect in the prospectus any facts or events arising
                     after the effective date of the registration statement (or
                     the most recent post-effective amendment thereof) which,
                     individually or in the aggregate, represent a fundamental
                     change in the information set forth in the registration
                     statement; and

               (iii) To include any material information with respect to the
                     plan of distribution not previously disclosed in the
                     registration statement or any material change to such
                     information in the registration statement.

     PROVIDED, HOWEVER, that paragraphs (a)(1)(i) and (a)(1)(ii) herein do not
apply if the information required to be included in a post-effective amendment
by those paragraphs is contained in periodic reports filed with or furnished to
the Commission by Chittenden pursuant to Section 13 or Section 15(d) of the
Exchange Act that are incorporated by reference in the registration statement.

          (2)  That, for the purpose of determining any liability under the
     Securities Act, each such post-effective amendment shall be deemed to be a
     new registration statement relating to the securities offered therein, and
     the offering of such securities at that time shall be deemed to be the
     initial bona fide offering thereof; and

          (3)  To remove from registration by means of a post-effective
     amendment any of the securities being registered which remain unsold at the
     termination of the offering.

     (b)  The undersigned Registrant hereby undertakes that, for purposes of
determining any liability under the Securities Act, each filing of Chittenden's
annual report pursuant to Section 13(a) or 15(d) of the Exchange Act that is
incorporated by reference in the registration statement shall be deemed to be a
new registration statement relating to the securities offered therein, and the
offering of such securities at that time shall be deemed to be the initial bona
fide offering thereof.

     (c)  Insofar as indemnification for liabilities arising under the
Securities Act may be permitted to directors, officers and controlling persons
of Chittenden pursuant to the foregoing provisions, or otherwise,

                                       3
<PAGE>

Chittenden has been advised that in the opinion of the Securities and Exchange
Commission such indemnification is against public policy as expressed in the
Securities Act, and is, therefore, unenforceable. In the event that a claim for
indemnification against such liabilities (other than the payment by Chittenden
of expenses incurred or paid by a director, officer or controlling person of
Chittenden in the successful defense of any action, suit or proceeding) is
asserted by such director, officer or controlling person in connection with the
securities being registered, Chittenden will, unless in the opinion of its
counsel the matter has been settled by controlling precedent, submit to a court
of appropriate jurisdiction the question whether such indemnification by it is
against public policy as expressed in the Securities Act and will be governed by
the final adjudication of such issue.

                                       4
<PAGE>

                                  SIGNATURES

     Pursuant to the requirements of the Securities Act of 1933, Chittenden
Corporation certifies that it has reasonable grounds to believe that it meets
all of the requirements for filing on Form S-8 and has duly caused this
registration statement (the "Registration Statement") to be signed on its behalf
by the undersigned, thereunto duly authorized, in the City of Burlington,
Vermont, on this 19th day of May 1999.

                                    Chittenden Corporation



                                    By: /s/ Paul A. Perrault
                                       ------------------------------------
                                       Paul A. Perrault
                                       Chairman of the Board, President and
                                       Chief Executive Officer


                               POWER OF ATTORNEY

     KNOW ALL BY THESE PRESENTS, that each individual whose signature appears
below hereby severally constitutes and appoints Paul A. Perrault and F. Sheldon
Prentice, and each of them singly, such person's true and lawful attorney-in-
fact and agent, with full power of substitution and resubstitution, for such
person and in such person's name, place and stead, in any and all capacities, to
sign this Registration Statement and any and all amendments (including post-
effective amendments) to this Registration Statement, and to file the same, with
all exhibits thereto, and all documents in connection therewith, with the
Securities and Exchange Commission, granting unto each said attorney-in-fact and
agent full power and authority to do and perform each and every act and thing
requisite and necessary to be done in and about the premises, as fully to all
intents and purposes as such person might or could do in person, hereby
ratifying and confirming all that said attorney-in-fact and agent or any
substitute or substitutes of any of them may lawfully do or cause to be done by
virtue hereof.

     Pursuant to the requirements of the Securities and Exchange Act of 1933,
this Registration Statement has been signed by the following persons in the
capacities and on the dates indicated.

<TABLE>
<CAPTION>
      Signature                     Capacity                              Date
      ---------                     --------                              ----
<S>                              <C>                                   <C>
/s/ Paul A. Perrault             Chairman of the Board, President      May 19, 1999
---------------------------
Paul A. Perrault                 and Chief Executive Officer
                                 (Principal Executive Officer)

/s/ Frederic H. Bertrand         Director                              May 19, 1999
---------------------------
Frederic H. Bertrand


/s/ David M. Boardman            Director                              May 19, 1999
---------------------------
David M. Boardman


/s/ Paul J. Carrara              Director                              May 19, 1999
---------------------------
Paul J. Carrara


/s/ Sally W. Crawford            Director                              May 19, 1999
---------------------------
Sally W. Crawford
</TABLE>

                                       5
<PAGE>

<TABLE>
<S>                              <C>                                   <C>
/s/ Richard D. Driscoll          Director                              May 19, 1999
---------------------------
Richard D. Driscoll


/s/ Lyn Hutton                   Director                              May 19, 1999
---------------------------
Lyn Hutton


/s/ Philip A. Kolvoord           Director                              May 19, 1999
---------------------------
Philip A. Kolvoord


/s/ James C. Pizzagalli          Director                              May 19, 1999
---------------------------
James C. Pizzagalli


/s/ Pall D. Spera                Director                              May 19, 1999
---------------------------
Pall D. Spera


/s/ Martel D. Wilson, Jr.        Director                              May 19, 1999
---------------------------
Martel D. Wilson, Jr.


/s/ Kirk W. Walters              Executive Vice President and          May 19, 1999
---------------------------
Kirk W. Walters                  Chief Financial Officer
                                 (Principal Financial and
                                 Accounting Officer)
</TABLE>

                                       6
<PAGE>

                                 EXHIBIT INDEX


Exhibit No.    Description
----------     -----------

     5.1       Opinion of F. Sheldon Prentice, as to the legality of the
               securities being registered.
    23.1       Consent of Arthur Andersen LLP.
    23.2       Consent of KMPG LLP.
    23.3       Consent of PricewaterhouseCoopers LLP.
    23.4       Consent of Counsel, F. Sheldon Prentice (included in Exhibit 5.1
               hereto).
    24.1       Power of Attorney (included on the signature page hereto).
    99.1       Vermont Financial Services Corp. Amended and Restated 1994 Stock
               Option Plan.  (Incorporated by reference to an attachment to the
               Proxy Statement filed by Vermont Financial Services Corp. on
               April 22, 1998).
    99.2       Eastern Bancorp, Inc. Stock Option Plan.  (Incorporated by
               reference to Exhibit 4.1 of the Registration Statement filed by
               Vermont Financial Services Corp. on Form S-8 (File No. 333-30251)
               on June 27, 1997).
    99.3       Vermont Federal Bank, FSB Stock Option Plan.  (Incorporated by
               reference to Exhibit 4.1 of the Registration Statement filed by
               Vermont Financial Services Corp. on Form S-8 (File No. 333-30251)
               on June 27, 1997).
    99.4       West Mass Bankshares, Inc. Stock Option Plan.  (Incorporated by
               reference to Exhibit 4.1.(d) of the Registration Statement filed
               by Vermont Financial Services Corp. on Form S-8 (File No. 33-
               58259) on March 24, 1995).

                                       7