Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of
1934

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[ ]Filed by a party other than the registrant


Check the appropriate box:
[ ]  Preliminary proxy statement
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                          OREGON TRAIL FINANCIAL CORP.
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               (Name of Registrant as Specified in Its Charter)

                          OREGON TRAIL FINANCIAL CORP
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                  (Name of Person(s) Filing Proxy Statement)

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Filed by Oregon Trail Financial Corp. pursuant to Rule 14a-12 under the
Securities Exchange Act of 1934, as amended.

                                   * * *


                ANNUAL MEETING TO BE HELD SEPTEMBER 28, 2001


Notice of Annual Shareholder Meeting
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     Oregon Trail Financial Corp. will hold its annual shareholder meeting at
10:00 a.m. PDT on September 28, 2001 at the Best Western Sunridge Inn and
Conference Center, One Sunridge Lane, Baker City, Oregon.  At this meeting,
shareholders will elect two directors, each to serve a three year term,
approve the appointment of Deloitte & Touche LLP as the Company's independent
auditors and consider any other matters to properly come before the meeting.
This meeting date is later than last year's because we needed additional time
to prepare materials in light of the opposition candidate(s) being proposed by
Joseph Stilwell.  Shareholders of record as of August 16, 2001 will be
entitled to notice of and to vote at the meeting.

Important Matters About Joseph Stilwell and the Stilwell Group
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     You may have received a letter from Joseph Stilwell and the Stilwell
Group in April of this year.  Over the last 12 months, Mr. Stilwell and the
Stilwell Group have purchased approximately 8.25% of the Company's outstanding
shares.  They want to force a quick sale of Oregon Trail and its 100-year old
community bank.  The Stilwell Group has announced that it intends to solicit
proxies from the Company's shareholders in support of its nominee(s) for the
Board.  Those persons, if elected, would replace one or both of the Company's
current directors standing for re-election.  If the Stilwell Group proceeds
with its solicitations, you will soon receive proxy materials from the
Stilwell Group, seeking support for its candidate(s).  You will also soon
receive proxy materials and other important information from the Board of
Directors about the annual meeting.

Please Wait For And Read Our Proxy Statement and Other Materials Before You
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Send in Your Proxy
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     This year's annual meeting will be important to all of our shareholders
and the many customers and communities we serve.  It may well determine our
future as an independent financial institution.  We will address the questions
raised in the proxy materials that you receive from the Stilwell Group.
PLEASE DO NOT SEND IN YOUR PROXY UNTIL YOU HAVE READ OUR RESPONSE.

     Please read your Board's proxy materials and other information carefully
before you vote your shares.  We believe the Stilwell Group's proxy materials
do not tell everything you need to know to make an informed decision about the
future of your Company.






     The Stilwell Group's proxy materials assert that current management is
not doing enough to maximize shareholder value, but we believe you should
consider these important facts:

*    Last year, your Board of Directors hired a new President, Berniel L.
     Maughan, and a new Chief Financial Officer, Jonathan McCreary.  During
     their first few months at Pioneer Bank, together with the existing
     management team they developed a multi-faceted plan to improve Company
     performance and enhance shareholder value.  They announced those
     initiatives on January 19, 2001.

*    For the fiscal quarter following the announcement of these initiatives
     ending March 31, 2001, OREGON TRAIL'S NET INCOME INCREASED 53% TO
     $849,000 OR $.26 PER SHARE compared to $557,000 or $.17 per share for the
     same period the year before.  Without the expenses caused by Stilwell and
     his many lawsuits aimed at gaining control of your Company, your
     COMPANY'S EARNINGS WOULD HAVE INCREASED 71%.

*    Earnings continued to improve during the first quarter of fiscal 2002
     ending June 30, 2001.  EARNINGS INCREASED 78% TO $.32 PER SHARE compared
     to the first quarter last year AND WOULD HAVE BEEN UP 100% if we did not
     have to incur further costs in responding to the Stilwell Group.

*    Excluding the expenses caused by the Stilwell Group, OREGON TRAIL'S
     RETURN ON EQUITY FOR OUR FIRST QUARTER OF FISCAL 2002 INCREASED 82% TO
     8.46%, a record high for your Company.

     These are just a few examples of the substantial improvements our
management team has achieved in the past year.  The Board has considered
various alternatives including the sale of the Company, BUT HAS CONCLUDED THAT
SELLING THE COMPANY AT THIS TIME WILL NOT MAXIMIZE SHAREHOLDER VALUE.

     If the Stilwell Group proceeds with its proxy solicitation, we will send
you additional information within a few days after its mailing.  PLEASE WAIT
UNTIL YOU RECEIVE OUR INFORMATION BEFORE YOU SUBMIT ANY PROXY.  Your vote will
be critical to your personal financial interests and the future of the
Company.

     SHAREHOLDERS SHOULD READ THE COMPANY'S DEFINITIVE PROXY STATEMENT WHEN IT
BECOMES AVAILABLE BECAUSE IT WILL CONTAIN IMPORTANT INFORMATION.  THE PROXY
STATEMENT AND OTHER RELEVANT DOCUMENTS WILL BE PROVIDED FREE TO ANY
SHAREHOLDER BY CALLING (541) 523-6327 OR WRITING THE COMPANY AT P.O. BOX 846,
BAKER CITY, OREGON 97814, ATTENTION PRESIDENT.  THE INFORMATION IS ALSO
AVAILABLE FREE FROM THE SECURITIES AND EXCHANGE COMMISSION'S WEBSITE AT
www.sec.gov.

August 21, 2001

Sincerely yours,

/s/Stephen R. Whittemore              /s/Berniel L. Maughan
Stephen R. Whittemore                 Berniel L. Maughan
Chairman of the Board                 President and CEO