Brattleboro
Trail Running Calendar near Brattleboro 2026-2027
Explore the top trail runs near Brattleboro for 2026-2027! We've gathered 6 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 fall fundraiser featuring a forested 5K and a half-mile Little Leaf Dash with family activities, prizes, a raffle, and on-site refreshments.
The Village Ultra is an Ultra Event in New Salem MA on October 11 2026, listed at 23 S Main St with coordinates 42.5002371, -72.3310936.
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 Mountain Park in Keene, NH, featuring four up and down loops, 1650 ft total ascent, and proceeds to 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.