Upton
Trail Running Calendar near Upton 2026-2027
Explore the top trail runs near Upton for 2026-2027! We've gathered 29 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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 community fundraiser on October 25, 2026 featuring a timed 5K trail, a 1K pre-teen road race, a 5K walk, children's games and a costume contest.
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.
Trail half marathon and 10.5K in Upton State Forest on November 8, with limited entries, aid stations, and post race amenities.
A family friendly run and walk at West Thompson Dam on November 8, 2026 featuring a timed 5K trail run, a 3K untimed walk and a free kids 1/4 mile run; proceeds support local trails, parks and a food pantry.
Trail races of 5.3 miles and 10 miles through Callahan State Park with road sections to and from Brophy Elementary in Framingham.
A multi terrain 5K, a scenic 2 mile walk and a kids loop at Old Sturbridge Village on November 15, 2026 with awards and participant shirts.
A scenic 5K trail run in Wrentham, MA on November 26, 2026 with awards, post-race donuts and cider, a raffle, and a $25 registration fee.