Sturbridge
Trail Running Calendar near Sturbridge 2026-2027
Explore the top trail runs near Sturbridge for 2026-2027! We've gathered 18 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A 5K trail race and 5K walk through Lake Street Park trails, plus a Kid Run on the lacrosse field for age 12 and under.
Lake Wallace Fall Fest on October 3, 2026 in Belchertown features a 5K, a 1K, and an accessible Roll & Stroll with vendors, music, and fundraising for trail accessibility.
October 4, 2026 NipMuck Trail Marathon in Ashford CT offers a 26.4 mile trail with rocks, roots and mud, plus a two person relay option.
A fall 5K and 2 mile walk at Ashley Reservoir in Holyoke supporting Legacy Equine Center & Sanctuary with scenic water views and local wildlife.
A community 5K in Bolton, CT on 10/17/2026 along the Hop River rails to trails, with a $30 entry donated to Project Purple to support pancreatic cancer awareness.
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
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 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.
A multi-distance event at Old Sturbridge Village featuring a 5K course that mixes road and trails, a scenic 2-mile walk, and a short kids trot.
March 2027
Trail race on March 28, 2027 in Union CT covering about 16 miles on the Nipmuck Trail through Yale Myers Forest with parking at Bigelow Hollow State Park.
May 2027
June 2027
Obstacle course weekend at Carter & Stevens Farm in Barre, MA featuring Sprint 5K, Super 10K, kids races, and wooded trails across pasture and cornfields.