Massachusetts
Massachusetts Trail Running Calendar 2026-2027
Explore the best trail runs in Massachusetts for 2026-2027! Our updated list features 53 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
A 6-hour weighted trail race on Mansfield’s WWII Veterans Memorial Trail where distance multiplied by carried weight determines the winner in Kz scoring.
A Fall River trailfest on October 17, 2026, with walks, runs, and a 10-mile ruck through the Bioreserve plus post-race music and family activities.
Fall trail race in Ravenswood Park with single track and carriage roads, part of the North Shore Trail Series, offering onsite registration and postrace baked goods and raffles.
A community 5K on October 18, 2026 supporting the Lincoln Land Conservation Trust with a scenic course, BYOB water policy, and environmental practices.
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.
Trail races at Mt. Tom State Park on October 24, 2026 offering 25k, 10k and 5k courses on technical, rocky fall trails with solo and two person relay options.
Timed trail challenge at Camp Greenough offering 5K, 10K or a six hour loop with run or ruck divisions and separate male and female rankings.
A backyard ultramarathon at Waters Farm with a one loop hourly race, a 4.2 mile community run, a free kids fun run, and a full festival day.
Free trail run at Caroline Tuthill Preserve in Edgartown featuring a 3.1 mile loop through pitch pine forest, salt marsh and a 160 foot boardwalk.
A rugged 5k trail run, ruck, and walk in Berkley MA on October 25, 2026 that honors military and first responder K9 teams while supporting local charities.
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.
A running event in Peabody MA on October 25, 2026 featuring a 5 km and a track 1 mile, with entry fees and Bermuda prize trips awarded to select finishers and raffles.
A community fundraiser on October 25, 2026 featuring a timed 5K trail, a 1K pre-teen road race, a 5K walk, children's games and a costume contest.
A fall festival in Tyngsboro featuring a 3K trail race, a free kids fun run for ages 7 and under, a farmer’s market, vendors, kids activities, and food on October 25.