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Trail Running Calendar near New Braintree 2026-2027

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Explore the top trail runs near New Braintree for 2026-2027! We've gathered 12 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

October 2026
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.
Backyard ultra and timed 6, 12, 24 and 48 hour races near Winchendon MA on a 4.1667 mile mixed terrain loop with pompom hats for participants.
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.
April 2027
Trail event in Hadley MA on April 25, 2027 with a 5K and a one mile Mushroom Mile, on-campus trails, a virtual 5K option, and proceeds to The Hartsbrook School.
May 2027
Run Across CT 123 is a 123 mile point-to-point ultramarathon from East Thompson to Southport with trail and road sections, aid stations, and a 36 hour cutoff.
A technical trail event on the Wapack Trail in Ashburnham MA offering 21.5, 43 and 50 mile options with rugged terrain and significant climbing.
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.
August 2027
A timed single-day endurance walk on Wachusett Mountain with 7, 14, 21, or 28 mile loops, optional weighted rucks, aid stations, and venue-specific finisher gear.
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