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Trail Running calendar near Winchester 2026-2027

We have found 83 Trailruns within 80 miles of Winchester. See below where and when you can find the races.

Catonsville High School XC Turkey Trot

Catonsville - 77 mi from Winchester

Run Thanksgiving at the 22nd Catonsville High School Turkey Trot featuring a chip timed 5K and 1 Mile Family Fun Run on a cross country course. Proceeds support CHS cross country and there are prizes; strollers and pets not allowed.

December 2026

Fall Backyard Burn Trail Run - Fountainhead

Fairfax Station - 52 mi from Winchester

Trail races at Fountainhead Regional Park on December 6, 2026 offer a 4.8 mile single loop and a 10.5 mile course that adds an out-and-back on the Bull Run Occoquan Trail, organized by EX2 Adventures with a charity partner.