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Trail Running Calendar near Pomfret 2026-2027

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Explore the top trail runs near Pomfret 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
A free 8-hour trail event in Tolland, CT where runners complete as many 3-mile loops on a marked 5K-ish course as they like, with provided food and a potluck.
A chip-timed 5K run/walk at Brimfield Winery on a two-lap grass course with hills, race swag, a wine pour, and age group awards; a one-lap 1.5 mile division is available.
A 5K cross country race at Waters Farm in Sutton Massachusetts that opens the USATF New England XC Grand Prix series. Separate men's and women's open races, on site registration, and a post race awards ceremony.
Ocean State Ultra in West Greenwich, Rhode Island (August 29–30, 2026) offers a 100 mile race with a 34 hour limit plus 12 and 6 hour loop events; registration runs March 30 to August 17, 2026.
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 5K trail race at Goddard Park in Warwick, RI on September 26, 2026, over fields and wooded trails along Greenwich Bay with onsite parking and age-group awards.
A trail event on the Moosup Valley State Park Trail featuring 5K, 8K, 10K and a Kids Fun Run. Parking and the finish are at Weidele's Pizza with post-race food, awards and a medallion or shirt option.
October 2026
A timed trail ultra in Cumberland RI offering 8 hour, 12 hour, and 34 hour options for individuals and teams up to four. The 4.2 mile loop mixes smooth trail and moderately technical rocky sections.
A 26.4 mile trail marathon in Ashford, CT on October 4, 2026 with rugged terrain and a two-person relay option.
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.
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.
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
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 on the Nipmuck Trail in Union CT with minimal aid stations, blue blazes, and proceeds supporting local trail stewardship.
April 2027
A point to point 123 mile ultramarathon across Connecticut on April 3, 2027, featuring trail and road sections, aid stations, five intermediate cutoffs and a 36 hour limit.
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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