Milton
Trail Running Calendar near Milton 2026-2027
Explore the top trail runs near Milton for 2026-2027! We've gathered 37 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Trail Animals Running Club stages a multi-distance trail event at Great Brook Farm State Park, from a free 0.5 mile youth run up to 50 miles, on marked looped courses.
Cross-country races at Great Brook Farm State Park in Carlisle MA on 09/13/2026, featuring a 2K youth race and multiple 5K fields as part of the USATF New England Grand Prix.
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.
October 2026
Timed trail event in Cumberland RI on a 4.2 mile loop offering 8 hour, 12 hour and 34 hour solo and team formats with distance awards and a large pit area.
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 run and fitness walk at Highland Park in Attleboro on October 4 2026. The traffic free grass course uses two laps of a 1.55 mile loop and includes a kids 100 yard dash plus a virtual 5K option.
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.
A 6 hour weighted trail race in Mansfield, MA where competitors carry and change weight each lap to score pound-miles called Kz on an out and back course.
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.
A community 5K in Quincy’s Merrymount Park with in-person and virtual options, raising funds for youth leadership, adult English classes, and mental health services for Asian and immigrant families.
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.
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.