Sturbridge
Trail Running Calendar near Sturbridge 2026-2027
Explore the top trail runs near Sturbridge for 2026-2027! We've gathered 11 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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 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.
November 2026
An annual festival at Brigham Hill Community Farm combining a community 5K and kids fun run with vendors, food, apple tastings, hayrides, and family activities.
Trail races in Upton State Forest offering a 10.5K and a two-lap half marathon over technical, hilly single-track and forest roads with limited fields.
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.
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.
March 2027
A roughly 16 miles trail race on the Nipmuck Trail near Bigelow Hollow State Park in Union CT with technical terrain, limited aid, and a waitlist.
May 2027
June 2027
Spartan obstacle races June 26 and 27, 2027 at a working dairy farm in Barre MA with Sprint 5 km, Super 10 km, and kids races.