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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.

October 2026
Trail ultra in Cumberland Rhode Island on Oct 3 and 4 2026 featuring a 5 mile loop and 34, 12, and 8 hour individual and team formats.
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.
October 4, 2026 NipMuck Trail Marathon in Ashford CT offers a 26.4 mile trail with rocks, roots and mud, plus 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.
A community 5K in Bolton, CT on 10/17/2026 along the Hop River rails to trails, with a $30 entry donated to Project Purple to support pancreatic cancer awareness.
A backyard ultramarathon at Waters Farm with a one loop hourly race, a 4.2 mile community run, a free kids fun run, and a full festival day.
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.
November 2026
A farm festival in North Grafton on November 1 with a 5K and kids run, apple tastings, hayrides, vendors, music, and activities supporting local hunger relief.
A community 5K trail run at East Greenwich High School supporting local families and charities with proceeds to EG Unified Sports Program, Women & Infants NICU and Give Kids The World.
Trail half marathon and 10.5K in Upton State Forest on November 8, with limited entries, aid stations, and post race amenities.
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.
A multi-distance event at Old Sturbridge Village featuring a 5K course that mixes road and trails, a scenic 2-mile walk, and a short kids trot.
An annual 5 km run and walk in Hopedale, MA that raises funds for local fire and police equipment and community programs.
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.
Trail race on March 28, 2027 in Union CT covering about 16 miles on the Nipmuck Trail through Yale Myers Forest with parking at Bigelow Hollow State Park.
April 2027
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
Point to point 123 mile ultramarathon across Connecticut from East Thompson to Southport with solo and relay options, 36 hour cutoff and mixed trail and road course.
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.
Elimination trail race near Big River Management Area in West Greenwich RI featuring repeated 3.8 mile loops with about 450 ft elevation gain per loop.
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