Our flagship fundraising event, the WSF Annual Charity Golf Tournament, is one of the most enjoyable and popular spring events in Winchester. Held in May, golfers from Winchester and beyond eagerly dust off their clubs to start the season at Winchester Country, a Donald Ross course renowned for its beauty and challenging layout.
Monday, May 11, 2026
- 10:00am – 11:45am: Tournament Check-in
- 12:00pm: Shotgun Start
- 6:00pm – 8:00pm: Dinner and awards presentation
The event sells out quickly, so if you are interested in playing this year, we encourage you to register early. The day of golf is followed by dinner and drinks at the Club, at which the Foundation presents the Sachem Spirit Award, honoring individuals who have had a significant impact on the high school athletic programs. In addition, two members of the Junior class at Winchester High School speak about their experience as student-athletes at the school.