Trail Running calendar near Windham 2026-2027

A weekend Spartan obstacle event at Sunflower Valley Farm on October 31 and November 1, 2026 featuring Sprint, Super, Kids races and Hurricane Heat formats across woods, mud and creek runs, with spectator access and medals for finishers.

Trail races at Red Wing Recreation Area in Lagrangeville, NY offering 100k, 50k and 10k looped courses with significant elevation. The 50k and 100k hold UTMB Index status and provide aid stations plus finisher medals.

A technical trail half marathon at Moreau Lake State Park near Gansevoort, NY, covering about 14 miles with 2700 feet of climbing and one aid station; start and finish are at the park beach.

This 8-hour timed trail run takes place on the rolling farm trails at Gurski Farm in Brookfield, CT. Runners complete as many laps as possible on a course featuring single track. It offers a community atmosphere where participants frequentl..

A trail 10k at Ward Pound Ridge Reservation plus a November virtual 100k challenge, with race results, photos, and a custom finisher woodallion for 100k finishers.

Trail race at Tarrywile Park in Danbury, CT, offering Marathon, Half Marathon and 10K on technical, hilly single-track trails with finisher medals, podium awards and a $600 half-marathon time bonus.

An annual Roxbury Road Runners charity race held on Thanksgiving Day, with proceeds supporting the Roxbury Scholarship Foundation and the Roxbury Ambulance Association. Results for the race are published as part of the club series.

Experience a 5K trail race through the scenic Stillwell Woods Preserve in Woodbury. This event honors the memory of Rob Lauterborn and supports the Center for Developmental Disabilities.

A late winter trail race at Gilbert Lake State Park on February 21, 2026 offering 50k, 25k, and 10k on a 6+ mile loop with a snow adjusted course and an aid station serving hot broth and snacks. Net proceeds support The Neighborhood Center.