Winchester
Trail Running Calendar near Winchester 2026-2027
Explore the top trail runs near Winchester for 2026-2027! We've gathered 32 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A harvest-season 5K trail event at White Barn Farm in Wrentham with off-road terrain, a midway water station, bib pick-up the day before, family Harvestween activities, and a portion of registrations donated to the local food pantry.
A fall trail event in Harvard on October 25, 2026 featuring a 5K through orchard and woods plus a 1 mile kids fun run, with age divisions, awards, shirts, and proceeds benefiting the Harvard Conservation Trust.
Stairs4RTroops at Gillette Stadium on October 25, 2026 is a stadium stair climb of about 5,184 steps that raises net proceeds for Homes For Our Troops.
Fall Festival and Pumpkin Run 3K at Innovation Academy in Tyngsboro features a professionally timed 3K, 30+ vendors, family activities, food, and a free kids fun run.
Trail races at Assabet River National Wildlife Refuge in Sudbury MA with 10K, 30K and a 6-hour timed loop event on dirt and gravel double-track trails.
A continuous 50-mile trail race on a 3.1-mile loop in Wrentham, MA, with chip timing, a 12-hour cutoff, and a 75-runner field limit.
November 2026
Two-day Spartan Stadion weekend at Fenway Park featuring a 5 km course with 20 obstacles, kids races, and spectator options.
November trail event at Willowdale State Forest offering looped distances from a free youth fun run to a 100K with fundraising for local land trusts.
Trail running in Hingham offering a single 4 mile loop, an eight hour loopathon, and a Backyard style hourly format with a lenient non elimination rule.
A hilly 5K at Pine Banks Park in Melrose supporting Melrose High School cross country teams, with overall and age group awards and post race refreshments.
Six-hour timed trail race on a 5K loop at Wright Locke Farm in Winchester MA with rocky rollers, a cupless barn aid station, and a youth discount.
Community 5K on Windham Woods School trails with a free kids fun run, raffle, awards, and on site lunch.
A community trail event at Good Pickin’ Farm with a scenic 5 mile run, a 2.5 mile walk or run, and a 1K kids run plus post race farm activities.
Trail races of 5.3 miles and 10 miles through Callahan State Park with road sections to and from Brophy Elementary in Framingham.
A community memorial run in Tyngsboro, MA with a 1.5-mile walk and two 5K options, raising funds for a school scholar/athlete award and science scholarships while maintaining a tradition of food donations.