Brookline
Trail Running Calendar near Brookline 2026-2027
Explore the top trail runs near Brookline for 2026-2027! We've gathered 41 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
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.
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 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 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 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.