Massachusetts
Massachusetts Trail Running Calendar 2026-2027
Explore the best trail runs in Massachusetts for 2026-2027! Our updated list features 63 exciting trail runs across the region. Find your next trail run in Massachusetts below and join the trail community at these great events!
September 2026
Cross country meet in Franklin Park with 5 km and 8 km races on September 19, 2026; entry fee $15 and minimum age 16.
A non-competitive women only 5K obstacle mud run at Carter & Stevens Farm in Barre, MA on September 20, 2026, featuring 18 plus obstacles and a teamwork focus.
A community run in Westford honoring a teen lost to domestic violence, featuring a 5K and a family fun run to raise funds for survivors.
Backyard Ultra in Leominster State Forest on September 26, 2026; runners repeat a 4.167 mile loop each hour until only one remains.
Trail races and a 6 hour timed event through Assabet River National Wildlife Refuge with aid stations, cupless rules, pacer options, and proceeds supporting refuge projects.
Community run at Shedd Park in Lowell offering 5K, 10K trail and a 1 mile kids fun run to support local conservation and education; donations matched dollar for dollar.
Holdenwood Trail Run 10K in Shirley MA is an early-fall charity race through fields, trails, forests and cobblestone bridges benefiting the Ayer-Shirley Education Foundation.
October 2026
An annual 5K cross country run or walk in Franklin Park supporting Boston Latin School Athletics. Team registration is new for 2026 and fees are tiered with free entry for BLS students.
A 5K trail race and 5K walk through Lake Street Park trails, plus a Kid Run on the lacrosse field for age 12 and under.
A community fall event at Lake Wallace in Belchertown with a 5K, an accessible 1K, a Roll & Stroll, vendors, live music, and donations to the Lake Wallace Gift Account.
Trail races in Groton Town Forest on October 4, 2026 offering 9.5 miles and 3.4 miles with a 250 participant limit and registration deadlines in September and October.
Join the annual Run Stanley event at Stanley Park for a variety of trail races including a 5K K9 run and an accessible 1 mile stroll. Support local wildlife sanctuary maintenance while enjoying a community day in the park.
A park-based, traffic-free 5K in Highland Park, Attleboro with a grass loop course, a kids 100 yard fun run, on-site activities, awards, and a virtual 5K option.
Trail races at Houghton's Pond in the DCR Blue Hills Reservation follow rolling dirt roads and forest paths with rocks and roots. Two distances are offered, about 7 miles and 3.7 miles, with notable elevation change on each course.
A fall 5K and 2 mile walk at Ashley Reservoir in Holyoke supporting Legacy Equine Center & Sanctuary with scenic water views and local wildlife.
A community cross-country festival in Wayland with youth 3 km races, open 5 km events, team awards, spectator-friendly courses, and a 5K that is part of the USATF-NE Grand Prix.
A community 5K and 1 mile fun run on October 11, 2026 supporting Unified programs at Beckwith and Dighton Middle Schools. Fees vary by registration period and registered runners receive T-shirts and awards for top finishers.
Clam Crawl in Barnstable MA on October 11 2026 offers 3 km and 7 km race options, funds three marine biology scholarships, and supports Cape Cod Roller Derby’s youth skating scholarship program. Entry is limited to 100 with online registration closin..
A time-based event in New Salem MA offering 12 hour and 24 hour run or walk options around the town common on October 11, 2026.