Massachusetts
Massachusetts Trail Running Calendar 2026-2027
Explore the best trail runs in Massachusetts for 2026-2027! Our updated list features 59 exciting trail runs across the region. Find your next trail run in Massachusetts below and join the trail community at these great events!
October 2026
Trail races through Powisset Farm and Noanet Woodlands in Dover MA with 8.6, 5.6, 3.1 and 1.5 mile options, post-race cider donuts and family activities.
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.
A stadium stair-climb at Gillette Stadium raising funds for Homes For Our Troops, covering about 5,184 steps in the lower bowl with individual, team, and fundraising options.
November 2026
Obstacle course weekend at Fenway Park with a Stadion 5 km featuring 20 obstacles, kids races and spectator access on November 7 and 8, 2026.
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 last runner standing backyard ultra on private farmland in Winchendon with a 4.1666 mile loop. The event also offers 6 hour, 12 hour and 24 hour timed options plus a standalone fastest lap competition.
Looped trail event at White Barn Farm on Nov 7, 2026, where runners complete 3.1 mile loops and choose how far to go.
Trail races in Upton State Forest offer 10.5K and half marathon options over technical, hilly single track and forest roads. The event has a 250 runner cap and aid stations spaced roughly every three miles.
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
Trail Animals Running Club hosts the TARC Winter Classic on December 5 in Middlesex Fells, offering 8, 32, and 40 mile looped trail races with marked Skyline Trail routes.
Celebrate the twentieth anniversary of this unique cross country race held at the Mount Hood Golf Club. Choose between a competitive three and a half mile run or a festive two mile walk through hilly terrain.
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.
March 2027
Trail races and a 1 mile Color Run in Salisbury on March 27, 2027, featuring 10K, 5K and a non timed color run, with proceeds supporting Salisbury Parks and Recreation.
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.
May 2027
A trail running event on the Wapack Trail in Ashburnham Massachusetts with 21.5 mile, 43 mile, and 50 mile options across rocky, technical terrain with aid stations, drop bag support, and a manual timing system.
June 2027
Point-to-point trail runs of 112 or 50 miles along the New England Trail blue blazes to Guilford, CT, requiring dedicated crews, navigation, and night trail experience.
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.
A two day Spartan obstacle event at Carter & Stevens Farm near Barre MA featuring Sprint 5 km, Super 10 km and kids races across wooded trails and open pastures.