Brattleboro
Trail Running Calendar near Brattleboro 2026-2027
Explore the top trail runs near Brattleboro for 2026-2027! We've gathered 7 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
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 in Brattleboro with a 5K trail run and a half‑mile Little Leaf Dash for children, plus fall activities and family amenities.
The Village Ultra is an ultra distance running event in New Salem MA on October 11 2026, held at 23 S Main St.
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 weekend at Kenty’s Farm with a 4.16667 mile loop, Last Runner Standing format, and timed 6/12/24/48-hour events plus themed community hours.