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Trail Running Calendar near Cumberland 2026-2027

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Explore the top trail runs near Cumberland 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 5K trail run at Goddard Park on September 26, 2026 featuring fields and wooded trails along Greenwich Bay, open to all ages with age group awards.
Trail races on the Moosup Valley State Park Trail with 5 km, 8 km, 10 km and a kids run plus post race food, awards and local charity support.
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.
October 2026
Second annual fall trail run and walk at Ryan Park in North Kingstown, RI; a 5K course with age group medals and proceeds benefiting the local firefighters association.
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.
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.
Trail races at Houghton's Pond in the DCR Blue Hills Reservation follow rolling dirt roads and forest paths with rocks and roots. Two distances are offered, about 7 miles and 3.7 miles, with notable elevation change on each course.
A spectator friendly cross-country festival in Wayland with three youth 3k races, two open 5k races, team awards, and USATF-NE Grand Prix status for the 5k.
A community 5K and 1 mile fun run on October 11, 2026 supporting Unified programs at Beckwith and Dighton Middle Schools. Fees vary by registration period and registered runners receive T-shirts and awards for top finishers.
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 Fall River trailfest on October 17, 2026, with walks, runs, and a 10-mile ruck through the Bioreserve plus post-race music and family activities.
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.
A rugged 5k trail run, ruck, and walk in Berkley MA on October 25, 2026 that honors military and first responder K9 teams while supporting local charities.
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 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 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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