<PAGE>   1
                       SECURITIES AND EXCHANGE COMMISSION

                              WASHINGTON, DC 20549
   
                                  FORM 10-K/A
                                (AMENDMENT NO.1)
    
                        FOR ANNUAL AND TRANSITION REPORTS
                     PURSUANT TO SECTIONS 13 OR 15(d) OF THE
                         SECURITIES EXCHANGE ACT OF 1934
   
MARK ONE)
[X]   AMENDMENT TO ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE
      SECURITIES EXCHANGE ACT OF 1934 (FILED DECEMBER 29, 1997)
    

For the fiscal year ended SEPTEMBER 30, 1997

[ ]   TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE
      SECURITIES EXCHANGE ACT OF 1934

For the transition period from _______ to _______

                         Commission file number 33-95962

                             CUMBERLAND FARMS, INC.
             ------------------------------------------------------
             (EXACT NAME OF REGISTRANT AS SPECIFIED IN ITS CHARTER)

                DELAWARE
      (STATE OR OTHER JURISDICTION                                              
    OF INCORPORATION OR ORGANIZATION)                         (I.R.S. EMPLOYER
  777 DEDHAM STREET, CANTON, MA  02021                       IDENTIFICATION NO.)
----------------------------------------                     -------------------
(Address of principal executive offices)                         04-2843586

REGISTRANT'S TELEPHONE NUMBER, INCLUDING AREA CODE (781) 828-4900

SECURITIES REGISTERED PURSUANT TO SECTION 12(B) OF THE ACT:

      TITLE OF EACH CLASS              NAME OF EACH EXCHANGE ON WHICH REGISTERED

              None
--------------------------------       -----------------------------------------

--------------------------------       -----------------------------------------

SECURITIES REGISTERED PURSUANT TO SECTION 12(G) OF THE ACT:

              None
---------------------------------------------------
                  (Title of class)

---------------------------------------------------
                  (Title of class)




         Indicate by check mark whether the registrant: (i) has filed all
reports required to be filed by Section 13 or 15(d) of the Securities Exchange
Act of 1934 during the preceding 12 months (or for such shorter period 


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that the registrant was required to file such reports), and (2) has been subject
to such filing requirements for the past 90 days. Yes  X   No 
                                                      ---     ---

         Indicate by check mark if disclosure of delinquent filers pursuant to
Item 405 of Regulation S-K is not contained herein, and will not be contained,
to the best of the registrant's knowledge, in definitive proxy or information
statements incorporated by reference in Part III of this Form 10-K of any
amendment to this Form 10-K. [X]

         Indicate by check mark whether the registrant has filed all documents
and reports required to be filed by Section 12, 13 or 15(d) of the Securities
Exchange Act of 1934 subsequent to the distribution of securities under a plan
confirmed by a court.

Yes  X    No 
    ---      ---

         As of December 22, 1997, the outstanding shares of each class of the
registrant's common stock* was as follows:

                  Class A Stock     8 shares
                  Class B Stock     121,014 shares

         *Neither class of stock is registered under the Securities Act of 1933,
as amended.










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<PAGE>   3



ITEM 7. MANAGEMENT'S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS
        OF OPERATIONS


RESULTS OF OPERATIONS

         The following table summarizes the results of operations for the fiscal
years ended September 30, 1997, 1996 and 1995, which is followed by Management's
Discussion and Analysis of Financial Condition and Results of Operations. The
financial information set forth below should be read in conjunction with the
Company's financial statements, related notes and other financial information
included elsewhere herein.
   
<TABLE>
<CAPTION>
                                                                      YEARS ENDED SEPTEMBER 30,               % INCREASE (DECREASE)
                                                                1997            1996            1995             1997       1996
                                                             ------------------------------------------       ---------------------
                                                                        In Thousands
<S>                                                          <C>             <C>             <C>                  <C>         <C> 
INCOME

  Retail Revenues                                            $1,149,987      $1,101,076      $1,059,011           4.4%        4.0%
  Other Income                                                   19,361          20,433          21,378          (5.2)%      (4.4)%
                                                             ----------      ----------      ----------         -----       -----
    Total                                                    $1,169,348      $1,121,509      $1,080,389           4.3%        3.8%

  Equity in earnings of Gulf Oil, L.P                             7,677           7,855          13,612          (2.3)%     (42.3)%
  Gains On sales of property and equipment                        8,782          11,372           9,673         (22.8)%      17.6%
                                                             ----------      ----------      ----------         -----       -----
    Total                                                     1,185,807       1,140,736       1,103,674           4.0%        3.4%

Wholesale revenues                                              299,298         274,635         240,835           9.0%       14.0%
                                                             ----------      ----------      ----------         -----       -----
Total income                                                  1,485,105       1,415,371       1,344,509           4.9%        5.3%
                                                             ----------      ----------      ----------         -----       -----
Costs and expenses
   Cost of sales                                              1,181,426       1,102,582       1,027,162           7.1%        7.3%
   Operating expenses                                           247,926         247,447         242,131           0.2%        2.2%
   Depreciation and amortization                                 22,299          18,703          17,541          19.2%        6.6%
                                                             ----------      ----------      ----------         -----       -----
    Total                                                     1,451,651       1,368,732       1,286,834           6.1%        6.4%
                                                             ----------      ----------      ----------         -----       -----

Operating income                                             $   33,454      $   46,639      $   57,675         (28.3)%     (19.1)%
                                                             ==========      ==========      ==========         =====       =====


OTHER OPERATING DATA

Merchandise gross profit                                     $  152,308      $  151,404      $  147,925           0.6%        2.4%

Merchandise gross profit as a percentage of sales                  29.8%           30.5%           29.9%

Gasoline gallons sold                                           501,050         493,623         470,576           1.5%        4.9%
Gasoline gross profit                                        $   58,470      $   63,947      $   65,737          (8.6)%      (2.7)%
Gasoline gross profit
  cents per gallon                                                 11.7            13.0            14.0         (10.0)%      (7.1)%

Operating income before depreciation and amortization
  as a percentage of total revenues                                 3.7%            4.6%            5.6%

Operating income as a percentage of total revenues                  2.2%            3.3%            4.3%

Comparable average store and station data:

  Merchandise sales growth                                          3.0%            0.5%            3.5%
  Gasoline gallons sold                                             1.5%            4.9%           10.3%

</TABLE>
    

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                                   SIGNATURES
   
     Pursuant to the requirements of Section 13 or 15(d) of the Securities
Exchange Act of 1934, as amended, the Registrant has duly caused this 10-K/A 
to be signed on its behalf by the undersigned, thereunto duly authorized, in
the City of Boston, Commonwealth of Massachusetts, on the 29th day of December,
1997.
    
                                   CUMBERLAND FARMS, INC.



                                   By: /s/ Lily H. Bentas
                                   ---------------------------------------------
                                   Name:  Lily H. Bentas
                                   Title: President, Chairperson of the Board of
                                          Directors and Chief Executive Officer


     Pursuant to the requirements of Section 13 or 15(d) of the Securities
Exchange Act of 1934, as amended, this report has been signed below by the
following persons on behalf of the registrant in the capacities indicated and on
the dates set forth opposite their names.

   
NAME:                                                              DATE:
-----                                                              -----

By: /s/ Lily H. Bentas                                            12/29/97
---------------------------------------------------               --------------
Name:   Lily H. Bentas
Title:  President, Chairperson of the
        Board and Chief Executive Officer



By: /s/ Kevin P. Johnson                                          12/29/97
---------------------------------------------------               --------------
Name:   Kevin P. Johnson
Title:  Vice president and Corporate Controller



By: /s/ Arthur G. Koumantzelis                                    12/29/97
---------------------------------------------------               --------------
Name:   Arthur G. Koumantzelis
Title:  Senior Vice President and
        Chief Financial Officer



By: /s/ John E. Burke                                             12/29/97
---------------------------------------------------               --------------
Name:   John E. Burke
Title:  Director
    


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By: /s/ Paul E. Hand                                              12/29/97
---------------------------------------------------               --------------
Name:   Dr. Paul Hand
Title:  Director



By: /s/ Byron Haseotes                                            12/29/97
---------------------------------------------------               --------------
Name:   Byron Haseotes
Title:  Director




---------------------------------------------------               --------------
Name:   Demetrios B. Haseotes
Title:  Director




---------------------------------------------------               --------------
Name:   George Haseotes
Title:  Director



By: /s/ James C. Mcdermott                                        12/29/97
---------------------------------------------------               --------------
Name:   James C. McDermott
Title:  Director



By: /s/ Dr. Geoffrey Pottow                                       12/29/97
---------------------------------------------------               --------------
Name:   Dr. Geoffrey Pottow
Title:  Director



By: /s/ Kenneth T. Koehler                                        12/29/97
---------------------------------------------------               --------------
Name:   Kenneth T. Koehler
Title:  Director

    
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