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CUSIP No. 685932105            SCHEDULE 14A                  Page 1 of 5
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                                  SCHEDULE 14A
                                 (RULE 14A-101)

                     INFORMATION REQUIRED IN PROXY STATEMENT
                            SCHEDULE 14A INFORMATION

                PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE
                         SECURITIES EXCHANGE ACT OF 1934

Filed by the registrant [ ]

Filed by a party other than the registrant [X]

Check the appropriate box:

[  ] Preliminary proxy statement.

[  ] Confidential, for use of the Commission only (as permitted by Rule
     14a-6(e)(2).

[  ] Definitive proxy statement.

[X ] Definitive additional materials.

[  ] Soliciting material under Rule 14a-12.

                          OREGON TRAIL FINANCIAL CORP.

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                (Name of Registrant as Specified in its Charter)


                        STILWELL VALUE PARTNERS II, L.P.
                            STILWELL ASSOCIATES, L.P.
                               STILWELL VALUE LLC
                                 JOSEPH STILWELL
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     (Name of Person(s) Filing Proxy Statement if Other Than the Registrant)


Payment of filing fee (check the appropriate box):

[X ] No fee required.

[  ] Fee computed on table below per Exchange Act Rules 14a-6(i)(1) and 0-11.

      (1) Title of each class of securities to which transaction applies:

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      (2) Aggregate number of securities to which transaction applies:

      (3) Per unit price or other underlying value of transaction computed
          pursuant to Exchange Act Rule 0-11 (set forth the amount on which the
          filing fee is calculated and state how it was determined):

      (4) Proposed maximum aggregate value of transaction:

      (5) Total fee paid:

[  ] Fee paid previously with preliminary materials.

[  ] Check box if any part of the fee is offset as provided by Exchange Act Rule
0-11(a)(2)  and  identify  the  filing  for  which the  offsetting  fee was paid
previously.  Identify the previous filing by registration  statement  number, or
the form or schedule and the date of its filing.

      (1) Amount Previously Paid:

      (2) Form, Schedule or Registration Statement No.:

      (3) Filing Party:

      (4) Date Filed:


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CUSIP No. 685932105            SCHEDULE 14A                  Page 3 of 5
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                   THE FOLLOWING ADVERTISEMENT APPEARED IN THE
         BAKER CITY HERALD AND LA GRANDE OBSERVER ON SEPTEMBER 19, 2001

                               The Stilwell Group
                             26 Broadway, 23rd Floor
                            New York, New York 10004
                              Phone: (212) 269-5800
                            Facsimile: (212) 269-2675
                             Email: Max OTFC@aol.com

Dear Fellow Oregon Trail Financial Corp. Shareholder:

NOTE: IMPORTANT  INFORMATION ABOUT THE GROUP'S WHITE AND BLUE PROXY CARD APPEARS
IN THE INSERT SENT TO YOU ON OR ABOUT  SEPTEMBER  17,  2001.  IF YOU  PREVIOUSLY
RETURNED A WHITE PROXY CARD AND WANT TO VOTE FOR THE GROUP'S  NOMINEE,  YOU MUST
RETURN A WHITE AND BLUE PROXY CARD INSTEAD.

In our Company's  fiscal year 2000 annual report,  Chairman of the Board Stephen
R. Whittemore  stated, "we continue to assess everything we do or do not do by a
major test of measurement: Is it in the best interests of our shareholders?" For
the entire 2001 fiscal year, the market price of the Company's  shares  remained
below the  Company's  book  value.  In fact,  the shares fell from above $18 per
share in  February  1998 to below $10 per share in January  2000 -- the price at
which they were offered for sale in our  Company's  initial  public  offering in
1997. I ask: How did the Board  respond to the bargain  value stock price?  Were
MORE shares repurchased than were being issued under the Company's  compensation
plans?  OOPS!  THE  COMPANY  ACTUALLY  ISSUED  MORE  SHARES  FOR THE  BENEFIT OF
EMPLOYEES AND DIRECTORS THAN IT REPURCHASED DURING FISCAL YEAR 2001. This, in my
estimation, was a major capital allocation blunder on our Board's part.

Two months  after my Group  filed a  statement  of the  Group's  desire that the
Company  maximize  shareholder  value,  the Company  announced  its January 2001
"Strategic  Direction and New Share Repurchase Plan". In management's own words,
"OTFC remains committed to increase earnings per share through stock repurchases
while shares trade at  significant  discounts  to book value and  purchases  are
anticipated  to be  accretive.  To this end,  the  Company's  Board of Directors
approved a new share  repurchase  plan to purchase of (sic) up to ten percent of
shares outstanding at its December meeting."

Since the January 2001  announcement,  the  Company's  shares have  continued to
trade at a significant discount to book value, and repurchasing more shares than
were  being  issued  under the  Company's  compensation  plans  would  have been
accretive  to book  value.  What  did the  Company  do?  OOPS!  DURING  THE LAST
REPORTING  PERIOD,  THE COMPANY  ACTUALLY  ISSUED MORE SHARES FOR THE BENEFIT OF
EMPLOYEES AND DIRECTORS THAN IT REPURCHASED. In my opinion, when those entrusted
to run our Company are unwilling -- or unable -- to fulfill their  promises,  it
is time for new blood on the Board.



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CUSIP No. 685932105            SCHEDULE 14A                  Page 4 of 5
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I think it is important for you to know that I believe that the Board's  attempt
to blame me for all of the Company's legal fees is unfounded.  The Company could
have  avoided a  significant  portion  of these fees had it not tried to keep me
from communicating with you on an equal footing.  They refused to comply with my
request under state law for the complete shareholder list.

The Company continues to retaliate against me. On Friday, September 7, 2001, the
Company  threatened to sue Mr.  Padrick,  my nominee for election as a director,
unless he dropped out of the election.  On Wednesday,  September 12, 2001, while
my and my lead counsel's offices in New York were closed, the Company filed suit
against  my Group  and Mr.  Padrick  in  federal  court in  Oregon.  (Additional
information  concerning  the  litigation  between  my Group and the  Company  is
included in the insert referred to above.)

To be clear: I am not trying to "force" or "control" anything. ALL I WANT IS FOR
ALL OF THE  SHAREHOLDERS,  NOT JUST THE BOARD AND ITS THIRD  MANAGEMENT  TEAM IN
THREE YEARS, TO HAVE A VOICE IN THE IMPORTANT DECISIONS ABOUT OUR COMPANY.  Your
vote for the Stilwell Group's nominee,  Kevin Padrick,  is a vote to elect a new
director to the Board who is "beholden" to ALL shareholders, and not a part of a
group of  directors  who  renominate  each other for  reelection  as their terms
expire  and who  "grandfathered"  a director  who moved out of the  market  area
specified in the Company's original bylaws by amending the bylaws retroactively.
I believe Mr. Padrick will do what's best for ALL shareholders by voting to:

     - sell the Company's  employee  vacation condo and stop the monthly fees to
       the directors for "overseeing" the condo;

     - strengthen the Board's oversight of management;

     - repurchase significant amounts of shares at prices below book value; and

     -  commence  the  process  of  exploring  a sale of the  Company at a price
        greater than book value.

I urge you to sign and  return the WHITE AND BLUE  PROXY  CARD  promptly  in the
envelope  provided  to you by my Group.  If you  receive  a proxy  card from the
Company,  please throw it away. I look forward to meeting with you if you attend
the annual meeting.

                                    Sincerely,

                                    /s/ Joseph Stilwell
                                    Joseph Stilwell
                                    On behalf of the Stilwell Group:
                                    STILWELL VALUE PARTNERS II, L.P.
                                    STILWELL ASSOCIATES, L.P.
                                    STILWELL VALUE LLC


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CUSIP No. 685932105            SCHEDULE 14A                  Page 5 of 5
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On August 16,  2001,  the  Stilwell  Value  Group (the  "Group")  filed with the
Securities  and  Exchange  Commission  (the  "Commission")  a  definitive  proxy
statement  in  connection  with the  election  of its  nominee  to the  board of
directors of Oregon Trail  Financial  Corp.  ("Oregon  Trail") at Oregon Trail's
2001 annual meeting of  stockholders.  Copies of the definitive  proxy statement
were mailed to stockholders on or about August 16, 2001.  Investors and security
holders  are  urged  to read  the  definitive  proxy  statement  and  additional
definitive  soliciting  material  because  they contain  important  information.
Investors and security  holders may obtain a free copy of the  definitive  proxy
statement  and other  documents  filed by the Group with the  Commission  at the
Commission's  website at www.sec.gov.  The definitive  proxy statement and these
other  documents may also be obtained for free by writing to Mr. Joseph Stilwell
at 26 Broadway, 23rd Floor, New York, New York 10004, or by contacting D.F. King
& Co. at (212) 269-5550.