Trail Running calendar near Freeport 2026-2027

A community fun run on 06/13/2026 behind Madbury Town Hall with a 1K kids run and a 5K route through Kingman Farm trails. Registration is free and donations for park improvements are accepted on the day.

A mountain footrace beside the Mount Washington Cog Railway offering a 2.75 mile summit climb or a 5.5 mile roundtrip, steep grades and boulder fields, and highly variable summit weather.

A six hour endurance event on a flat 4 mile rail trail loop in Poland, Maine, where participants run as many loops as they wish and recorded mileage is recognized; shirts included with paid entry.

A timed 5K loop through woods and fields at the Maine Outdoor Wellness Center on June 20, 2026. Bibs, water, snacks, and family activities are provided and a $15 registration supports community building and programming.

Field & Forest 5 Miler is a roughly 5 mile trail race on the Crystal Spring property in Brunswick, ME. The mostly off pavement course has single track and wood bridges, and the field is limited to 50 runners.

A trail 5 km race at Libby Hill Forest Trails in Gray, ME on June 21, 2026. Online registration is $15 through June 19, race day registration is $20 and students enter free. Proceeds support trail maintenance and door prize drawings are pla..

A community trail event in Freeport, Maine on June 21, 2026 featuring a 5K loop through the school property plus a one mile kids run, part of Faith Fest with free registration from May 20 to June 21.

A small weeknight trail race series around Portland Maine from June 25 to July 30 2026, featuring races of about 5K to 6.5 miles, capped fields, partnerships with local land trusts, and series prizes for those who complete three races.

A single-day endurance walk on Cranmore Mountain with looped distances from 7 to 28 miles, optional weighted rucking, timed tracking, aid stations, and mountain views over North Conway and the White Mountains.

Second annual Kennebec Savings Bank East Bayside Trail Fest in Portland on June 28 2026 offers three trail events plus a post event celebration with music, food trucks and local beer. Proceeds support Portland Trails and the Bicycle Coaliti..

A women only 5K obstacle mud run with 18+ obstacles at Hemond's MX & Offroad Park in Minot, Maine on June 28, 2026. Open to females aged seven and up who may run, jog, or walk the course.

A family oriented 5k on July 4 in Tamworth that begins at historic Ordination Rock, tours village streets and museum trails, includes a bandana, ice cream and a bib raffle, and supports the Tamworth Outing Club.

A backyard ultra on Portland's Back Cove Trail featuring repeated 4.16 mile loops along a tidal estuary. Two aid stations, on site personnel, free adjacent parking, and volunteer support are provided; refunds are restricted.

A summit mountain trail race at Loon Mountain of about six miles with roughly 3,000 feet of gain, including a steep 1 km section up to 40 percent. The event is part of the USATF-NE circuit and offers over $20,000 in cash prizes.

A 9 mile two lap trail race on Bradbury Mountain featuring hilly, technical single track and classic Maine rocks and roots. The field is limited to 160 runners and the race has a 3 hour cutoff.

Tough Mountain Challenge is a 5K obstacle race at Sunday River in Newry, Maine on July 25, 2026. The course features mud, water, walls and woods and the weekend includes a slopeside music party and lodging discounts.

Trail runs in White Mountain National Forest near Chatham NH featuring a 29 KM two loop option and a 14 KM single loop that cross the Baldfaces. Both routes require mandatory safety gear and involve significant elevation gain with limited a..

A roughly 3.8 mile trail race at Kingman Farm in Madbury, NH on July 26, 2026, featuring rolling nordic style paths and switchback singletrack; proceeds support the Doug Flutie Jr. Foundation for Autism and day of registration is available.

A 5 km trail race at Scribner's Mill on the Crooked River in Harrison, Maine. Pine-lined singletrack and river views, with proceeds supporting Loon Echo Land Trust.

The event is cancelled. It had been planned as a 10K ruck obstacle course at Pineland Farms in New Gloucester, Maine, featuring The Crucible with 20+ obstacles and prize rules requiring participants to ruck the full course with a pack.