Wellesley
Trail Running Calendar near Wellesley 2026-2027
Explore the top trail runs near Wellesley for 2026-2027! We've gathered 45 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A 3 mile in person trail run in the Fells for women and nonbinary people, run at a conversational pace around the North Reservoir in Winchester, MA.
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
Test your endurance on a five mile trail loop in Rhode Island with 8 hour, 12 hour, and 34 hour options for individual runners and teams.
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.
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.
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.
Test your strength and speed in this unique six hour weighted race where your total distance is multiplied by the weight you carry on a historic memorial trail.
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 backyard ultramarathon at Waters Farm where runners do a 4.167 mile loop each hour until one remains, accompanied by a community 4.2 mile run and a family festival.
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.