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Trail Running Calendar near Sutton 2026-2027

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Explore the top trail runs near Sutton for 2026-2027! We've gathered 35 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.
Trail races and a 6 hour timed event through Assabet River National Wildlife Refuge with aid stations, cupless rules, pacer options, and proceeds supporting refuge projects.
Holdenwood Trail Run 10K in Shirley MA is an early-fall charity race through fields, trails, forests and cobblestone bridges benefiting the Ayer-Shirley Education Foundation.
October 2026
Test your endurance on a five mile trail loop in Rhode Island with 8 hour, 12 hour, and 34 hour options for individual runners and teams.
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.
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 park-based, traffic-free 5K in Highland Park, Attleboro with a grass loop course, a kids 100 yard fun run, on-site activities, awards, and a virtual 5K option.
A community cross-country festival in Wayland with youth 3 km races, open 5 km events, team awards, spectator-friendly courses, and a 5K that is part of the USATF-NE Grand Prix.
Experience a point to point trail race in Northeast Connecticut on the Airline Trail. Choose between marathon, half marathon, and 10K distances with individual or relay team options to support local student education.
Test your strength and speed in this unique six hour weighted race where your total distance is multiplied by the weight you carry on a historic memorial trail.
A harvest-season 5K trail event at White Barn Farm in Wrentham with off-road terrain, a midway water station, bib pick-up the day before, family Harvestween activities, and a portion of registrations donated to the local food pantry.
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.
Trail races through Powisset Farm and Noanet Woodlands in Dover MA with 8.6, 5.6, 3.1 and 1.5 mile options, post-race cider donuts and family activities.
A fall trail event in Harvard on October 25, 2026 featuring a 5K through orchard and woods plus a 1 mile kids fun run, with age divisions, awards, shirts, and proceeds benefiting the Harvard Conservation Trust.
A stadium stair-climb at Gillette Stadium raising funds for Homes For Our Troops, covering about 5,184 steps in the lower bowl with individual, team, and fundraising options.
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.
A continuous 50-mile trail race on a 3.1-mile loop in Wrentham, MA, with chip timing, a 12-hour cutoff, and a 75-runner field limit.
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