Boston
Trail Running Calendar near Boston 2026-2027
Explore the top trail runs near Boston for 2026-2027! We've gathered 31 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Obstacle course weekend at Fenway Park on November 7 and 8 2026 featuring a Stadion 5 km with 20 obstacles plus kids races and spectator access.
A November trail festival at Willowdale State Forest in Ipswich offering multiple looped distances from a 10K to 100K, a Cider Donut Mile, and a flagged 0.5‑mile youth run, with cupless aid stations and fundraising for local land trusts.
A 6 hour timed trail race on a 5K loop at Wright Locke Farm in Winchester Massachusetts, featuring rocky rolling singletrack, a barn aid station in a cupless format, and provisions for adaptive athletes and youth discounts.
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.
December 2026
February 2027
Experience a winter trail challenge at Hale Education featuring 15 mile and 30 hour options. Navigate three unique loops through the Massachusetts woods while testing your endurance and self reliance in cold weather conditions.
April 2027
10 mile trail race on April 10, 2027 in Andover MA along the Merrimack River with aid stations, handmade prizes, and proceeds supporting trail maintenance.
The TARC Spring Classic takes place April 24, 2027 in Jericho Town Forest, Weston, MA, with 10K, half marathon, marathon and 50K looped trail options, a single aid station, marked course, and a cupless race format.
June 2027
A 20 miles single loop hike through Wompatuck State Park near Boston on June 5, 2027 with aid stations, a finisher medal and a personalized certificate.