Brookline
Trail Running Calendar near Brookline 2026-2027
Explore the top trail runs near Brookline for 2026-2027! We've gathered 42 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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.
Community 5 mile trail run at Lynn Woods Reservation with a no drop pace, Norvan trail vest demos, post-run refreshments, and free parking.
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 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 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.
A fall festival in Tyngsboro featuring a 3K trail race, a free kids fun run for ages 7 and under, a farmer’s market, vendors, kids activities, and food on October 25.
Trail races at Assabet River National Wildlife Refuge in Sudbury MA with 10K, 30K and a 6-hour timed loop event on dirt and gravel double-track trails.
A continuous 50-mile trail race on a 3.1-mile loop in Wrentham, MA, with chip timing, a 12-hour cutoff, and a 75-runner field limit.
November 2026
Obstacle-course weekend at Fenway Park with a Stadion 5 km (20 obstacles), kids races and spectator access on November 7-8, 2026.