Brattleboro
Trail Running Calendar near Brattleboro 2026-2027
Explore the top trail runs near Brattleboro for 2026-2027! We've gathered 8 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
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
Inaugural trail event in Dublin NH with a 5K and a 1 mile kids fun run on October 10, 2026 supporting the Dublin Consolidated School PTO.
A fundraising event at the Winston Prouty Center in Brattleboro with a 5K trail run, a half mile Little Leaf Dash, family activities, and refreshments.
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 5K technical trail run at the Chris Lewit Tennis Academy in South Londonderry, Vermont, through wooded laps by the West River with proceeds benefiting veterans charities.
A 5-mile mountain trail race at Granite Gorge with four laps and about 1650 feet of elevation, held to benefit the Keene Community Kitchen.
November 2026
A backyard ultra style last runner standing event in Winchendon MA on a 4.1667 mile loop with multiple timed formats and a fastest lap option.