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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 37 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
A 5K cross-country race at Waters Farm in Sutton MA, the first stop in the USATF New England XC Grand Prix with pre-registration $35 and day of $40.
A multi-format ultrarunning event in West Greenwich RI with a 100 mile race and timed 12 hour and 6 hour loop events.
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 one mile obstacle course in Warren, RI with two giant mud pits, kids play area, food and giveaways. Proceeds support Thrive Outside and its programs to expand youth access to nature.
Cross country meet in Franklin Park with 5 km and 8 km races on September 19, 2026; entry fee $15 and minimum age 16.
Ocean State 5K Trail Run at Goddard Park in Warwick, RI on September 26, 2026 features a fast, flat 5K along the bay and grasslands with on-site vendors and amenities.
Trail races on the restored Moosup Valley State Park Trail in Sterling CT with 5K, 8K, 10K and a kids fun run plus postrace food and shirt or medallion options.
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
A 5K fall trail run and walk at Ryan Park in North Kingstown on October 3, 2026, benefiting the North Kingstown Firefighters Association. Registrations before September 14 include a race day t shirt and top finishers receive medals.
Timed trail event in Cumberland RI on a 4.2 mile loop offering 8 hour, 12 hour and 34 hour solo and team formats with distance awards and a large pit area.
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 5K run and fitness walk at Highland Park in Attleboro on October 4 2026. The traffic free grass course uses two laps of a 1.55 mile loop and includes a kids 100 yard dash plus 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.
On October 11, 2026 the HFC Striders Cross Country Festival returns to Wayland for its 20th running, featuring 3K youth races across age groups and two 5K open races, with awards and proceeds benefiting Wayland High School.
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.
Six hour weighted trail race on Mansfield's WWII Veterans Memorial Trail where competitors carry chosen weight over repeated laps to score pound miles (Kz).
United We Move Trailfest on October 17, 2026 in Fall River offers trail walks, runs and a 10 mile ruck with post-event music, refreshments, and a food truck ticket.
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.
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