Trail Running calendar near Chatham 2026-2027

Bradbury Badass Races in Pownal ME use a 15.5 mile singletrack loop offered as a Half Pint 25K or a Pounder 50K two lap option, with two aid stations, a 10 hour race cutoff, and a 100 runner cap per race.

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.

Experience the summit of Mount Agamenticus with a 5K or 1 mile trail race. Support local conservation efforts while running or hiking through Maine trails and participate in a raffle for all entrants.

Experience a scenic run through wooded conservation trails finishing at the Hooksett Public Library. This community event features a 5K trail race and a half mile kids fun run to support local youth programs.

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.

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.

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.

A virtual 55K challenge linked to the Great Bay 5K in Stratham, New Hampshire. Complete 55 kilometers in one day or between October 1 and October 24, 2026; registration includes a shirt if ordered by October 1 and a bib with a beer or cider..

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.

Experience the Bobcat Ridge 25K trail race at the Edwin L Smith Preserve in Maine. This event features a limited field of 100 runners and supports the Kennebunkport Conservation Trust.

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.

Vulcan's Fury Trail Race at Pawtuckaway State Park offers a half marathon and a 5 Miler over technical trails with boulder fields, switchbacks, stream crossings and a rocky ridge called the Devil's Staircase. Three aid stations support runn..

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.