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
A fall 5K and 2 mile walk at Ashley Reservoir in Holyoke supporting Legacy Equine Center & Sanctuary with scenic water views and local wildlife.
Cross-country festival in Wayland with youth 3 km races and open 5 km races, team competitions and awards on a course through fields and wooded trails.
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 Event in New Salem MA on October 11 2026, listed at 23 S Main St with coordinates 42.5002371, -72.3310936.
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.
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.