Trail Running calendar near Freeport 2026-2027

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

The 26th North American Wife Carrying Championship returns to Sunday River in Newry, Maine on October 10, 2026. Teams of one man and one woman race a 278 yards obstacle course with log hurdles, a sand trap, and the Widow Maker water hazard.

A technical trail race at Pawtuckaway State Park on October 11, 2026, offering a half marathon and a 5-mile course with $7,500 in prize money. The routes cross boulder fields, single-track trails and a rocky slope called the Devil's Stairca..

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.

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.