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CUSIP No. 685932105            SCHEDULE 14A                 Page 1 of 10
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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.

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

                (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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CUSIP No. 685932105            SCHEDULE 14A                 Page 2 of 10
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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 10
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                               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 ENCLOSED INSERT.  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.

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




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CUSIP No. 685932105            SCHEDULE 14A                 Page 4 of 10
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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 enclosed insert.)

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. 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,

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

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

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CUSIP No. 685932105            SCHEDULE 14A                 Page 5 of 10
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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.




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CUSIP No. 685932105            SCHEDULE 14A                 Page 6 of 10
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                      IMPORTANT INFORMATION CONCERNING THE
          GROUP'S WHITE AND BLUE PROXY CARD AND THE PARTIES LITIGATION

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.  (the  "Company") at its 2001 annual
meeting of stockholders. Copies of the definitive proxy statement were mailed to
stockholders  on or about  August 16, 2001.  This  information  supplements  the
definitive proxy statement. 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.

THE WHITE AND BLUE PROXY CARD

The Company's  Board currently  consists of six members.  Two seats on the Board
are up for election at the Annual  Meeting.  As we  previously  advised you, the
Group is seeking to elect Mr. Kevin D. Padrick to fill one of the open  director
seats,  in  opposition  to one of the Company's  nominees.  We  previously  also
advised  you that we would vote for the  election  of one of the  Company's  two
nominees, using the White Proxy Card previously sent to you. On August 29, 2001,
we sent you a new WHITE AND BLUE PROXY CARD which authorizes a vote ONLY for the
Group nominee and NOT for either Company  nominee.  When we mailed you the WHITE
AND BLUE PROXY CARD,  we informed you that we still would vote WHITE PROXY CARDS
up to 24.9% of the  outstanding  shares of the Company  for the  election of our
nominee and one of the Company nominees.

In accordance  with Office of Thrift  Supervision  rules, we have now determined
that the WHITE PROXY CARD will not be used at all. Therefore,  if you previously
returned a WHITE PROXY CARD and want to vote for the Group's  nominee,  you must
return  the WHITE AND BLUE  PROXY  CARD.  If you return the WHITE AND BLUE PROXY
CARD,  your vote will only  count for our  nominee,  Kevin D.  Padrick.  In that
event,  your vote will NOT count towards the election of any Company nominee and
you will not be able to vote for either Company  nominee.  To vote for either or
both of the Company's nominees,  you must return the Company's GREEN PROXY CARD,
which would preclude you from voting for the Group's nominee,  unless you attend
the meeting in person.  If you have already returned a WHITE AND BLUE PROXY CARD
and have not subsequently  revoked it or sent a GREEN PROXY CARD to the Company,
you do not need to do anything further to vote for the Group's nominee.

UPDATE ON THE PARTIES' LITIGATION

On September  12, 2001,  the  Multnomah  County  Circuit  Court for the State of
Oregon orally granted Charles Rouse's motion for summary judgment.  The Group is
disappointed  by the  decision  and  presently  intends to file an appeal at the
appropriate time.


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CUSIP No. 685932105            SCHEDULE 14A                 Page 7 of 10
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Also on September 12, 2001,  the Company  filed a lawsuit  against the Group and
Kevin  Padrick in the United  States  District  Court for the District of Oregon
alleging that the Group and Mr. Padrick violated the federal  securities laws by
making materially misleading  statements in our proxy materials.  The suit seeks
injunctive  relief.  The  Group  intends  to  defend  the  action  and  to  file
counterclaims  against the Company for making  allegedly false statements in its
proxy materials.

The suit alleges that several  statements in the Group's previous letters to you
were  materially  misleading.  For example,  the suit alleges that the following
statement is false and materially misleading:

      "We also learned through discovery that Director Charles H. Rouse,  having
      found it `hard to make a viable business work in rural Oregon,' liquidated
      his business `Rouse Home Furnishing' in November 1995. (Mr. Rouse recently
      started a new career as a real estate salesman in Portland.)"

The Company  alleges that the Group's  statement  "juxtaposes  and  inaccurately
paraphrases selected excerpts from Mr. Rouse's testimony" and "suggests that Mr.
Rouse  is not a  successful  business  operator"  and  that he  "liquidated  his
business at a loss and moved to Portland for a more lucrative  opportunity." For
purposes of completeness,  we quote below the testimony from which the quotation
was taken:

      "Q. And then what  happened in November of '95 with that  business  [Rouse
      Home Furnishing]?
      A.   It's when I closed it out.
      Q.   What does that mean, closed it out?
      A.   I just sold out, had a big QB sale.
      Q.   A what sale?
      A.   Quitting business sale.
      Q.   And why did you quit business in November of '95?
      A. I had toyed  with the idea of selling  it. I talked to a couple  people
      and I seen it's hard to make a viable business work in rural Oregon. And I
      thought  if  anybody's  going to lose my money it will be me.  You have to
      sell them on contract.  You've seen that many times. It was easier to take
      my money and run, so I did."

The  Company  also  takes  issue  with the  statement  that "the  Board  members
automatically  re-elect  THEMSELVES  every year." The statement was not meant to
suggest that shareholders have been disenfranchised -- obviously the Company has
annual meetings where shareholders,  not directors,  vote on the election of the
directors.  However,  the Board's  nominating  committee  consists of the entire
Board and does not include any independent members. The nominating committee has
re-nominated  directors as their terms expire each year since the Company became
public.

The Company also objects to the statement  that "the Company's  Directors  award
themselves  free shares and free options on shares every year." To clarify,  the
directors have not "paid" for the


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options  and  restricted  shares  granted to them in October  1998 other than by
continuing  to serve on the Board.  Each director also receives at least $18,400
per year in cash fees as  compensation  for their  services  as  directors.  The
options  granted to directors (for 23,474 shares per person at an exercise price
of $11.15 per share) vest in four equal annual installments beginning in October
1999 and the  restricted  shares  (9,389  shares per person)  vest in four equal
annual installments also beginning in October 1999. I note that the only mention
of these awards to directors in the Company's  proxy  statements  since 1998 are
general  references in the  beneficial  stock  ownership  table each year and in
Appendix A to the proxy  statement  for this year's annual  meeting,  not in the
discussion  under  "Director's  Compensation"  as  required  by the SEC's  proxy
disclosure  rules.  Also,  although the  shareholders  approved the compensation
plans under which these  awards were made at the annual  meeting  held in August
1998, they did not  specifically  approve the proposed grants to directors.  The
plans  expressly  reserve the power to grant awards  thereunder to the Board and
the Board has the authority to make  additional  awards to officers,  employees,
and non-employee directors in its sole discretion at any time.

                                      *****

Again, to vote for Kevin Padrick, the Group's nominee, you MUST return the WHITE
AND BLUE PROXY CARD.  If you have not  already  done so, we urge you to sign the
enclosed card and send it back today in the enclosed postage-paid envelope.


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CUSIP No. 685932105            SCHEDULE 14A                 Page 9 of 10
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                                    P R O X Y

         THIS PROXY IS SOLICITED BY THE STILWELL GROUP IN OPPOSITION TO
             THE BOARD OF DIRECTORS OF OREGON TRAIL FINANCIAL CORP.

                          OREGON TRAIL FINANCIAL CORP.

                       2001 ANNUAL MEETING OF SHAREHOLDERS

The undersigned  hereby  appoints  Joseph Stilwell and Spencer L. Schneider,  or
either of them, as proxies with full power of substitution,  to vote in the name
of and as proxies for the undersigned at the 2001 Annual Meeting of Oregon Trail
Financial Corp. (the "Company"),  and at any  adjournment(s) or  postponement(s)
thereof, according to the number of votes that the undersigned would be entitled
to cast if personally present on the following matters:

1.  ELECTION  OF  DIRECTORS  - To elect  KEVIN D.  PADRICK as a director  of the
    Company

             -- FOR                 -- WITHHOLD

To withhold  authority to vote for the election of Kevin D. Padrick,  place an X
next to Withhold or strike out Mr. Padrick's name above.



2.  APPOINTMENT  OF  DELOITTE & TOUCHE LLP AS  INDEPENDENT  ACCOUNTANTS  FOR THE
    FISCAL YEAR ENDING MARCH 31, 2002:

                  For     Against     Abstain
                     ----        ----        ----

IMPORTANT: PLEASE SIGN AND DATE ON THE REVERSE SIDE.

This proxy, when properly executed,  will be voted in the manner directed herein
by the undersigned Shareholder.  UNLESS OTHERWISE SPECIFIED,  THIS PROXY WILL BE
VOTED  "FOR"  THE  ELECTION  OF THE  GROUP  NOMINEE  AS  DIRECTOR  AND "FOR" THE
APPOINTMENT  OF DELOITTE & TOUCHE LLP THE INDEPENDENT ACOUNTANTS.  This proxy
revokes all prior proxies given by the undersigned.

In their discretion, the proxies are authorized to vote upon such other business
as may properly come before the meeting,  or any  adjournments or  postponements
thereof,  as provided in the proxy statement provided herewith.  The proxies may
exercise  discretionary  authority  only as to  matters  unknown  to the Group a
reasonable time before their proxy solicitation.

Please  sign  exactly  as  your  name  appears  hereon  or on your  proxy  cards
previously sent to you. When shares are held by joint tenants, both should sign.
When  signing as an attorney,  executor,  administrator,  trustee,  or guardian,
please  give  full  title  as  such.  If a  corporation,  please  sign  in  full
corporation  name by the  President  or  other  duly  authorized  officer.  If a
partnership,  please sign

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CUSIP No. 685932105            SCHEDULE 14A                 Page 10 of 10
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in partnership name by authorized person.  This proxy card votes all shares held
in all capacities.

                                            Dated:
                                                  -----------------------------

                                                  -----------------------------
                                                                (Signature)

                                                  -----------------------------
                                                  (Signature, if jointly held)

                                            Title:
                                                  -----------------------------


               PLEASE SIGN, DATE, AND MAIL THIS PROXY CARD TODAY.