Trail Running calendar near Kennebunkport 2026-2027

A recurring, in-person group trail run for women and nonbinary people around the North Reservoir in Winchester, MA, covering a conversational 3 mile loop at about 11 to 12 minutes per mile. Sessions are led by local run leaders and cancel f..

A 23K mountain trail race in Tamworth, New Hampshire, with about 4,800 feet of climbing and a route over the 3,478 foot summit of Mount Chocorua. The race is part of the White Mountain Endurance Cup series.

A two-lap mountain race at Mount Sunapee Resort on June 7, 2026, covering about 9.3 miles and 3,300 feet of climbing. The event hosts the 2026 USATF Mountain Running Championships and the Collegiate Mountain Running Nationals with cash priz..

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 second annual trail event in Dunstable, Massachusetts offering a 5 mile loop or a six hour race of repeated 5 mile loops. The course follows an old railroad bed, an arched stone bridge, woods, peaks, and single track trails.

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 5.6 K trail run and walk at Berry Pond in Harold Parker State Forest on June 14, 2026. Walkers and leashed dogs are welcome; prizes are awarded, all entrants receive a bandana, and hotdogs are provided after the race.

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 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.

A trail half marathon in Lynn Woods Reservation on June 21, 2026, run as three identical loops over forested singletrack and carriage roads. The event emphasizes environmental stewardship and uses a centralized start and finish at the main..

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.