Trail Running calendar near Brattleboro 2026-2027

A 26.4 mile trail marathon in Ashford Connecticut with a two person relay option. The route follows a 13 mile segment of the Nipmuck Trail and relies on blue blazes for navigation.

Enjoy autumn trails at the Keene Family YMCA Fall Foliage Trail Races on October 4, 2026, with 5K and 10K options around scenic Keene, NH. Run for community impact while enjoying chip timed courses and seasonal views.

Point to point UTMB Index ultratrail across central Massachusetts with 100 mile, 50 mile and 50 kilometer options, wave starts, and seeded pacing to coordinate aid station support.

Join the 20th Wayland / HFC Striders Cross Country Festival on October 11, 2026, featuring youth 3K races and open 5K events that support Wayland High School cross country and track. Presented by Middlesex Savings Bank with awards and commu..

Tackle the Trail on October 17, 2026 is a point to point trail race along the Air Line Trail State Park between Willimantic and Putnam. Distances include marathon, relay marathon, half marathon and 10K with four staffed relay stations.

A multi distance trail event on October 17 and 18, 2026 in Brookline NH along the Granite Town Rail Trail, featuring a 30 hour ultramarathon and a 30 mile night race. All profits support local trail conservation.

A mountain race in Keene, NH featuring four repeated climbs and descents on mostly ski trails and some single-track, totaling 4.9 miles and 1650 feet of elevation. Proceeds support the Keene Community Kitchen and prizes are awarded.

A trail half marathon at Moreau Lake State Park in Gansevoort, NY, covering roughly 14 miles and 2700 feet of gain on technical singletrack with one aid station near Bonita Lake.

TARC Winter Classic offers 8 32 and 40 mile trail races on the rugged Middlesex Fells Skyline Trail with roots, rocky climbs and occasional Boston skyline views. Affordable entry and proceeds support land conservation.

Krampuslauf at Dartmouth Skiway brings a Central European Krampus run to New England with 5K, 10K, and a 9 hour 10K lap option. Finishers receive medals and lap runners earn pins and a 50K medal.