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Trail Running Calendar near Thompson 2026-2027

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Explore the top trail runs near Thompson for 2026-2027! We've gathered 20 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
An ultramarathon weekend in West Greenwich featuring a revised 10-mile loop and events including 100 mile, 12 hour, and 6 hour formats.
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.
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.
October 2026
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 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.
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.
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.
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
Looped 3.1 mile trail at White Barn Farm with a stocked aid station and cumulative distances from 5K to 50K.
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
Trail races at Monastery Trails in Cumberland, RI on March 14, 2027 offer distances from a 1 mile kids run to a 100K 12 hour ultra. Team ultra entries and a multilap 5 hour option are available and all finishers receive a medal.
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
A point to point 123 mile ultramarathon across Connecticut from East Thompson to Southport with trails, roads, aid stations, and a 36 hour cutoff.
An obstacle course race in Cumberland, Rhode Island featuring a 3.2 miles course with about 1,000 feet elevation, multiple wave formats including elite and age group competition, multilap sessions, and a 12 hours ultra option.
May 2027
A looped hill endurance event in Cumberland Rhode Island where participants run or hike as many laps as possible within a 12 hour period. The top male and female who cover the greatest distance are named King and Queen of the Hill.
June 2027
The inaugural F.I.T. 50k in Cumberland, Rhode Island is a 50k trail ultramarathon with equal parts smooth non technical and moderately technical terrain. The event includes a generous cutoff time and a $65 registration fee.
An iterated loop endurance race in West Greenwich RI where runners repeat a 3.8 mile loop with 450 ft of climb and must complete each loop within 60 minutes until only one runner remains ready to continue.
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