Brattleboro
Trail Running Calendar near Brattleboro 2026-2027
Explore the top trail runs near Brattleboro for 2026-2027! We've gathered 10 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
An inclusive trail festival at Northfield Mountain offering a 20k prediction run, an untimed 5k fun run/hike (about 6k), a kid's run, and a virtual option.
September 2026
Pisgah Mountain Trail Races in Chesterfield, NH offers 50k and 23k mountain trail ultraruns on Sunday 9/13/26. Aid stations provide LMNT, Tailwinds, and Untapped and proceeds support New Hampshire Special Olympics.
A 1 mile inflatable fun run and walk at Butterfield Park in Orange, MA raising funds for Fisher Hill School sixth grade trip fundraising, with advance registration at $15.
A community 5K in Jaffrey, NH offering a woods trail and a rail trail out and back. Proceeds support the volunteer Jaffrey Firefighters Company and equipment needs of the Jaffrey Fire Department.
October 2026
Fourth annual CLTA 5K honors a Purple Heart recipient and USAF Major General with a trail course through fall foliage near Manchester, Vermont.
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.
A 4.9-mile mountain trail race at Granite Gorge Mountain Park in Keene, NH with 1,650 ft of elevation gain; proceeds benefit the Keene Community Kitchen.
November 2026
A last runner standing backyard ultra on private farmland in Winchendon with a 4.1666 mile loop. The event also offers 6 hour, 12 hour and 24 hour timed options plus a standalone fastest lap competition.