Trail Running calendar near Randolph 2026-2027

A three-day Scottish heritage festival at Loon Mountain Resort in mid September featuring music, Highland Dance, heavy athletics, sheep dog trials, seminars and family programming.

An unmarked trail event on Kilkenny Ridge in Stark, New Hampshire, offering 50 mile, 25 mile and 25K courses with significant elevation gain, backcountry aid stations, required mandatory gear, and navigation using GPS tracks.

Pair up for a three hour endurance relay on a two mile loop of trails and fields. Alternate laps with your partner to accumulate the maximum distance possible in this team based challenge.

A community-focused mountain running event in East Charleston, Vermont on September 26, 2026, crossing five peaks on mainly single-track trails. Timed full marathon and 20 mile trail only options are offered while proceeds support NorthWood..

A trail event in Arundel, Maine on September 26, 2026 featuring 5k, 10k and half marathon routes through the ACT and Eastern Trails. All entrants receive a medal and a t shirt, and there is a free kids bike race.

Experience the inaugural Cirque Series at Jay Peak featuring a 7.1 mile course with over 3000 feet of vertical gain. Runners navigate technical terrain and rocky ridges to reach the summit for 360 degree views of the Vermont landscape.

Trail ultrarunning at Wolfe's Neck Farm in Freeport, ME on September 27, 2026. The course is a roughly five mile loop on dirt roads and forest trails with bridges, stairs, and roots, offered in 10, 30, and 50 mile formats plus relays.

Hit the Trail 2026 offers a timed 5K run/walk or bicycle rides on Vermont's scenic Lamoille Valley Rail Trail. The event raises funds for healthy aging services in Central Vermont. Join the community in Morrisville on September 27 for a day..

Experience an annual half marathon on the tallest mountain in Southern Maine. Run across technical single track and mountain ridges to support local land conservation and trail maintenance.

Last person standing trail running on October 3, 2026 in Center Conway, New Hampshire. Runners repeat a roughly 3.5 mile loop with about 250 feet of climb per lap; camping and weekend meals are available.

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.

Trail races at Trapp Family Lodge in Stowe, VT on Oct 17, 2026 include a half marathon and a full marathon that is two laps of a 13.1 mile loop with singletrack, dirt roads and steep climbs to Round Top Mountain.

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.

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.

Race Mozey brings the Central European Krampus Run tradition to New England. Choose from a 5K, 10K, or a 9-hour challenge to complete laps at the Dartmouth Skiway. Finishers get medals, and the event supports Vermont Adaptive Ski and Sports..