Sturbridge
Trail Running Calendar near Sturbridge 2026-2027
Explore the top trail runs near Sturbridge for 2026-2027! We've gathered 15 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 26.4 mile trail marathon in Ashford CT on October 4, 2026 with a two person relay option and a course of rocks, roots, mud, and wood bridges.
A fall 5K and 2 mile walk at Ashley Reservoir in Holyoke supporting Legacy Equine Center & Sanctuary with scenic water views and local wildlife.
Backyard ultramarathon at Waters Farm with a 4.167 mile hourly loop, a 4.2 mile community run, a free kids fun run, and a full 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.
November 2026
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 roughly 16 mile out and back trail race on the Nipmuck Trail in Union CT with minimal aid and proceeds supporting local trail stewardship.
April 2027
June 2027
An obstacle race weekend at Carter & Stevens Farm in Barre MA featuring a Sprint 5K with 20 obstacles, a Super 10K with 25 obstacles, and kids races.