Trail Running calendar near Portland 2026-2027

Join the Black Bear Trail Races in New Hampshire's scenic Waterville Valley. Choose from four trail distances, including a 50K with major mountain climbs. All runners receive a finisher's medal and finish near the Town Square.

Experience the largest climb in GBF history at Mount Washington in New Hampshire. Choose between ten and twenty mile routes while carrying a twenty pound load through significant elevation gains.

The Five Fields Farm Races offer a scenic 50K and a challenging 10K on the trails of Maine's Bald Pate and Holt Pond Preserves. Both courses start and finish at the farm's apple orchard. All event proceeds support local land conservation.

Test your endurance at Pineland Farms in Maine with this backyard ultra trail race. Run a 4.2 mile loop through pristine wooded trails and see how many laps you can complete in this last person standing format.

Experience a flat and non technical trail race at Cherry Hill Farm in Gorham Maine. Choose between 50k 25k or 10k distances consisting of multiple loops around the scenic farm property.

Experience an untimed trail run through the woods of western Maine featuring 3.6 mile laps of forest roads and single track. Enjoy on site camping and wood fired pizza along the scenic shores of Mirror Lake.

The Megunticook Trail Festival offers three distinct trail races in Maine's scenic Camden Hills State Park. Choose from a tough 10K, a gravel-trail 20K, or a comprehensive 50K that covers most of the park's trails. Experience runs where the..

The Kismet Cliff Run is a September trail race in New Hampshire's White Mountains. Choose the brutally scenic Beast of the East half marathon or the technical Little Beast 5 miler. This event is part of the 2026 Skyrunner USA Series, featur..

Event Overview The Big Brad Ultras is a trail ultramarathon event. It takes place on the trails of Bradbury Mountain State Park and the surrounding area in Maine, USA. Course Details The event uses a 16.5-mile loop course. This loop is run..

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 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.

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.

Experience a trail-only loop course through Wolfe's Neck Center and Freeport Conservation Trust. This cup-less event offers distances from 10 to 50 miles on a scenic route featuring dirt roads, woods, and local bridges.

This 21k trail race ascends Pleasant Mountain in Bridgton, Maine, featuring technical single-track and a ridge traverse. The event includes an afterparty with food, drinks, and music. All proceeds support local land conservation efforts.

Experience a scenic downhill course along the shores of Great Bay or take on the virtual 55K challenge. Support local estuary conservation while enjoying a community race that includes a long sleeve shirt and a post race beverage.

Experience the ultimate test of endurance in Center Conway at this last person standing ultramarathon. Run a scenic 3.5 mile forest loop every hour until only one participant remains.

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.