Sturbridge
Trail Running Calendar near Sturbridge 2026-2027
Explore the top trail runs near Sturbridge for 2026-2027! We've gathered 19 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A community fundraiser in Pomfret Center with a trail 5K and a 0.5 mile kids run supporting the Pomfret Community School PTO. Early and later registration fees differ and awards plus finisher medals are given.
A non-competitive women only 5K obstacle mud run at Carter & Stevens Farm in Barre, MA on September 20, 2026, featuring 18 plus obstacles and a teamwork focus.
Backyard Ultra in Leominster State Forest on September 26, 2026; runners repeat a 4.167 mile loop each hour until only one remains.
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.
A community fall event at Lake Wallace in Belchertown with a 5K, an accessible 1K, a Roll & Stroll, vendors, live music, and donations to the Lake Wallace Gift Account.
Experience the NipMuck Trail Marathon in Ashford, a 26.4 mile course featuring technical terrain and a relay option through the scenic woods of Connecticut.
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 where runners do a 4.167 mile loop each hour until one remains, accompanied by a community 4.2 mile run and a family festival.
A multi-terrain 5K, a scenic 2 Mile walk, and a short kids loop at Old Sturbridge Village on October 25, 2026, with event shirts, limited medals, and age-group prizes.
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
Harvest Home Festival in North Grafton with a 5K Farm Run; 5K registration includes festival admission and proceeds support Community Harvest Project programs.
Trail races in Upton State Forest offer 10.5K and half marathon options over technical, hilly single track and forest roads. The event has a 250 runner cap and aid stations spaced roughly every three miles.
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.
March 2027
A 16 mile trail race on the Nipmuck Trail in Union, CT on March 28, 2027, organized by the Shenipsit Striders with minimal aid and proceeds supporting local trail groups.
April 2027
June 2027
Obstacle course weekend at Carter & Stevens Farm in Barre MA with Sprint, Super, and kids races plus spectator access on June 26 to 27, 2027.