Trail Running calendar near Freeport 2025-2026

Celebrate the season with the Jackson 5k Turkey Trot and kids 1k on scenic trails in Jackson, New Hampshire. This family friendly event brings the community together while raising funds for Jackson Grammar School and Girls on the Run.

Tackle the Chocorua Mountain Race, a rugged 23 km trail in the White Mountains with steep climbs, rocky singletrack and a summit loop over Mount Chocorua. Limited to 250 entrants, this demanding course packs 4,500 feet of elevation.

Explore scenic trails south of Sebago Lake at the inaugural Otter Pond Trail Races in Standish, Maine on June 13, 2026. Choose a timed endurance Dawn to Dusk challenge, a 10K or a kids run while supporting Bonny Eagle Athletics.

Race The Cog invites runners to tackle the Mount Washington summit via the historic Cog Railway tracks on June 20, 2026, with 2.75 or 5.5 mile options. Expect steep, rocky terrain and a summit Cog train return for the shorter course.

Tackle steep ledges, exposed scrambles and single track trails at the Baldface Scramble in Chatham NH on July 25, 2026. Choose a demanding 14K single loop or a 29K double loop with a Mount Meader summit; mountain experience is required.

Jigger Johnson Ultras in Waterville Valley offers rugged White Mountain trail runs of 100, 50 and 20 miles with alpine summits and serious climbing. Courses are mostly unmarked so bring navigation skills and mountain safety gear.

Firebird Trail Races in Windham Falmouth Maine feature 50K, marathon and 13M races on technical single track through Lowell Preserve. Tackle rocky, root strewn trails with friendly aid stations and earn a carved wood Firebird medal.

Run the Black Bear Trail Races in Waterville Valley New Hampshire on August 29 2026, with options from a 1 Mile fun run to a mountain 50K across scenic peaks. All finishers get a commemorative award and postrace snacks for every level.

Run the Megunticook Trail Festival in Camden Hills State Park on Sep 12, 2026, with 50K, 20K and 10K options across rocky summits, ocean views and classic Maine woodland trails. Entries are limited so register early.

Enjoy scenic 1 Mile and 5K trail runs and hikes at the Annual Trail Challenge on Mount Agamenticus in York, Maine Saturday September 19. Proceeds support conservation and education and a community raffle makes the day festive.