Wayland
Trail Running Calendar near Wayland 2026-2027
Explore the top trail runs near Wayland 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.
October 2026
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 multi format trail event on the Granite Town Rail Trail in Brookline and Milford NH on October 17 and 18 2026, featuring 7.5 mile relays, 15 mile and 30 mile races and a 30 hour ultramarathon. Proceeds support local trail conservation.
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 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.
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.