Trail Running calendar near Freeport 2026-2027

A mountain trail event in North Conway offering a technical 5 mile Little Beast and a half marathon Beast of the East with significant vertical gain and exposed alpine sections. Part of the SKYRUNNER USA Series.

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.

Experience a historic celebration of Scottish heritage at Loon Mountain Resort featuring heavy athletics, stone lifting, and traditional music amidst New Hampshire's scenic fall foliage.

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 the natural beauty of Maine by running or walking through woodland trails in Arundel. This conservation focused event offers 5k, 10k, and half marathon distances along with a kids bike race and live music.

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.

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.

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.