Boston
Trail Running Calendar near Boston 2026-2027
Explore the top trail runs near Boston for 2026-2027! We've gathered 38 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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.
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.
Trail race in Ravenswood Park on October 18, 2026 featuring single track and carriage roads plus race day registration and post-race baked goods.
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.
Community trail run from Marathon Sports Wellesley to Norumbega Reservoir with Topo Ultraventure 5 demos, sauna and cold plunge, plus coffee and breakfast.
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.