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Trail Running Calendar near Sterling 2026-2027

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Explore the top trail runs near Sterling for 2026-2027! We've gathered 23 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 free 3 mile out-and-back beach run at Westerly Town Beach held at low tide. The community event is organized by the Westerly Track Club and the Stavros family as a memorial run.
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.
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.
October 2026
Trail races at Bradford Preserve on October 3, 2026 feature 5K, 10K and a free kids run on dirt trails with seasonal course markings and a required orange clothing rule per state regulations.
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 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 fall trail event at Grills Preserve in Westerly with 10 mile and 10 km courses across single-track trails and riverfront sections. Club timing is used, orange clothing is required, and post-race refreshments are provided.
November 2026
A Thanksgiving themed chip timed 5k at Stonington Vineyards on November 8, 2026. The event features vineyard scenery and includes a t shirt, a portable wine glass, a finisher medal that doubles as a wine stopper and a wine pour.
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 November trail race at Burlingame State Park offering 4 mile and 8 mile courses on dirt trails and roads, a required orange garment mandate, post-race food, and age group awards for both distances.
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.
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