Trail Running calendar near Windham 2026-2027

A 23 km lollipop trail race in the White Mountain National Forest with about 4,500 feet of gain and a 3,478 foot summit on technical, rocky trails. Mandatory mountain gear is required and participants should have prior hilly trail experienc..

A 6 mile trail race at Bradbury Mountain in Pownal, Maine, featuring single and double track trails with rolling hills, a 1 hour 48 minute cutoff, limited fields, race shirts at pickup, and prizes from sponsor donations.

A ninth annual trail race through Dogtown Common on a rugged 5.4 mile course that mixes carriage roads and technical rock sections. Walkers are welcome, course maps are available, and prizes and event shirts are offered.

A 6.9 miles mountain trail race at Cannon Mountain, New Hampshire with 3,080 ft of elevation gain and a summit at 4,031 feet. The route features a 2 mile Kinsman Ridge section on steep technical trails and a strict 2 hour summit cutoff.

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.

Teams are driven blindfolded several miles to an unknown location, then must navigate back to the start by the shortest route. This free team event uses cross country scoring and prohibits GPS, phones, and running on I 95 or I 495.

A mountain trail race from the Mount Washington Cog Railway base to the summit in Bretton Woods, NH, with a 2.75-mile summit option (train descent) or a 5.5-mile roundtrip.

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.

A women only 5K obstacle mud run at Kimball Farm in Haverhill, MA on June 21, 2026. The course features 18 plus obstacles and welcomes participants age 7 and up with an emphasis on fun and teamwork rather than competition.

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.

A charity team challenge on June 27, 2026 in Bristol, NH that recreates Special Forces mission tasks. Teams of 6–12 choose Operator or Recruit levels, with awards for top teams, MVPs, fundraising leaders, and participant milestones.

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.