Massachusetts
Massachusetts Trail Running Calendar 2026-2027
Explore the best trail runs in Massachusetts for 2026-2027! Our updated list features 67 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 community cross-country 5K at Franklin Park on October 3, 2026, open to Boston Latin School affiliates and local runners and walkers with team options and tiered fees.
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.
Lake Wallace Fall Fest on October 3, 2026 in Belchertown features a 5K, a 1K, and an accessible Roll & Stroll with vendors, music, and fundraising for trail accessibility.
Run the winding single lane trails of Groton Town Forest with a choice of 9.5 mile or 3.4 mile courses featuring roots, rocks and rolling climbs. Limited to 250 runners, this community race supports Groton trail maintenance and finishes with snacks.
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.
Community 5 mile trail run at Lynn Woods Reservation with a no drop pace, Norvan trail vest demos, post-run refreshments, and free parking.
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 spectator friendly cross-country festival in Wayland with three youth 3k races, two open 5k races, team awards, and USATF-NE Grand Prix status for the 5k.
A 5K and 1 Mile Fun Run at the Dighton Rehoboth High School cross country course raising funds for student Unified programs, with early registration and event awards.
Beach fun run at Sandy Neck Beach with 3K and 5K options that raises funds for marine biology scholarships and local youth programs.
The Village Ultra is an ultra distance running event in New Salem MA on October 11 2026, held at 23 S Main St.
10 km trail race in Milton MA on 10/11/2026 featuring a moderately technical, low elevation course; registration runs 9/25 to 10/11, fee $20.
A six hour weighted trail race in Mansfield MA where competitors carry and adjust weight each lap and score by pound miles called Kz.
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.
Trail race in Ravenswood Park on October 18, 2026 featuring single track and carriage roads plus race day registration and post-race baked goods.
A community 5K on October 18, 2026 supporting the Lincoln Land Conservation Trust with a scenic course, BYOB water policy, and environmental practices.