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Trail Running Calendar near Brimfield 2026-2027

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Explore the top trail runs near Brimfield 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.

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.
September 2026
A 56 mile end to end run along the Farmington Canal Heritage Trail from West Suffield to New Haven raising funds for Mental Health Connecticut.
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 women only 5K obstacle mud run at Carter & Stevens Farm in Barre, MA on September 20, 2026. The course has 18+ obstacles, welcomes participants ages seven and up, and emphasizes teamwork over competition.
October 2026
A 26.4 mile trail marathon in Ashford, CT on October 4, 2026 with rugged terrain and a two-person relay option.
Join the annual Run Stanley event at Stanley Park for a variety of trail races including a 5K K9 run and an accessible 1 mile stroll. Support local wildlife sanctuary maintenance while enjoying a community day in the park.
A time-based event in New Salem MA offering 12 hour and 24 hour run or walk options around the town common on October 11, 2026.
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 race at Mt. Tom State Park on October 24, 2026, with single and relay options from 5k to 25k on rugged single-track terrain. The event supports Kestrel Land Trust and includes aid stations, medical crews, and awards.
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
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
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.
June 2027
Point-to-point trail runs of 112 or 50 miles along the New England Trail blue blazes to Guilford, CT, requiring dedicated crews, navigation, and night trail experience.
A two day Spartan obstacle event at Carter & Stevens Farm near Barre MA featuring Sprint 5 km, Super 10 km and kids races across wooded trails and open pastures.
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