Trail Running calendar near Greenwood 2026-2027

A 25K trail race at the Edwin L. Smith Preserve in Kennebunkport, Maine on October 3, 2026, with proceeds to the Kennebunkport Conservation Trust. Registration is limited to 100 entrants and includes a shirt if registered by September 5.

The Mile for Mentoring will take place in Gilford on Sunday 4 October 2026.

Devil's Den Ultra in Bradford, Vermont on Oct 10 to 11 2026 uses a 10K loop on Wrights Mountain and offers 30 hour, 12 hour and 10K options. Entries are capped at 100 and finishers receive tarot style awards.

Teams compete on a 278 yard obstacle course featuring hurdles and a water hazard. This unique event in the Maine mountains rewards the winners with their partner's weight in beer and five times their weight in cash.

A mixed human powered 100k in Norway, Maine combining 25 km of trail running with 75 km of biking across six preserves. Solo and duo options are available and proceeds benefit TruStrength Tomorrow and Western Foothill Land Trust.

The Cranmore Mountain Race is a classic two lap mountain run in New Hampshire. Runners tackle ski slopes and trails for a share of $7500 in prizes. This historic event is part of the USATF New England Mountain Circuit.

Trail race at East Windham Conservation Area offering a five loop 50k and a single loop 10k. The course uses Purple Red and Blue trails with two aid stations per loop and about 900 feet of climb per lap.

Experience a timed mountain trek across the rugged ridges of Vermonts Northeast Kingdom. Choose from multiple loop distances and the option to carry weighted gear for an added challenge on the scenic trails of Burke Mountain.

Discover the beauty of Emmons Preserve at a community event featuring trail races and family activities. Enjoy music and local treats while supporting holistic education through a variety of distances for runners and walkers.

Nighttime mountain races at Cranmore Resort on November 7, 2026 featuring 5 km and 10 km courses, reflective markers, required headlamps, and post-event pizza and awards.

A trail 5 km Turkey Trot and a 1 km kids fun run in Jackson New Hampshire on November 27, 2025, staged at the Eagle Mountain House lower fields. The course runs through local nordic trails and supports school and youth running programs.