Wellesley
Trail Running Calendar near Wellesley 2026-2027
Explore the top trail runs near Wellesley 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 6-hour weighted trail race on Mansfield’s WWII Veterans Memorial Trail where distance multiplied by carried weight determines the winner in Kz scoring.
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 with a one loop hourly race, a 4.2 mile community run, a free kids fun run, and a full festival day.
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
A farm festival in North Grafton on November 1 with a 5K and kids run, apple tastings, hayrides, vendors, music, and activities supporting local hunger relief.
Trail event in Cumberland RI on November 1, 2026 with a kids 1 mile, a 5k, a 5 mile technical trail and a 4 hour multi lap option.
Obstacle-course weekend at Fenway Park with a Stadion 5 km (20 obstacles), kids races and spectator access on November 7-8, 2026.
A November trail event in Hingham MA offering a single 4 mile loop, an open 8 hour loop-count race, and a Backyard style hourly format that allows missed cutoffs.
Trail half marathon and 10.5K in Upton State Forest on November 8, with limited entries, aid stations, and post race amenities.
A hilly 5K at Pine Banks Park in Melrose supporting Melrose High School cross country teams, with overall and age group awards and post race refreshments.