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

November 2026
A multi terrain 5K, a scenic 2 mile walk and a kids loop at Old Sturbridge Village on November 15, 2026 with awards and participant shirts.
The Hopkinton Turkey Trot on November 21 in Hopkinton, MA offers 10K, 5K and a Little Locals 1K with proceeds supporting Family Reach and Hopkinton High School.
An annual 5 km run and walk in Hopedale, MA that raises funds for local fire and police equipment and community programs.
A scenic 5K trail run in Wrentham, MA on November 26, 2026 with awards, post-race donuts and cider, a raffle, and a $25 registration fee.
Trail trail races in Cumberland RI on Nov 28, 2026 with a kids 1 mile, 5k, 5 mile and a 4 hour multi lap option using chip timing.
December 2026
Trail event in Cumberland, RI offering kids 1 mile, 5K, 5 mile and a 4 hour multi lap with chip timing and marked courses.
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 technical terrain, minimal aid stations, and 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.
A 123 miles point to point ultramarathon across Connecticut from East Thompson to Southport, with trail and road sections, a 36 hour cutoff, and relay and 100K options.
May 2027
Community 3.1 mile race and 1 mile kids run in Columbia CT benefiting Horace W. Porter eighth grade class on a mixed road and trail 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.
An elimination style trail race in West Greenwich, RI on a 3.8 mile loop with 450 ft of gain per lap where runners must finish each loop in under 60 minutes to continue.
October 2027
Trail races on the Airline Trail in Northeast Connecticut with marathon, half marathon, 10K and an up to five person marathon relay; proceeds support local students.
Test your endurance on a scenic 5K trail loop in Wrentham where you decide how far to go one hour at a time with distances ranging from 5K to 50K.
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