Trail Running calendar near Kennebunkport 2026-2027

A 5.4 mile trail race through Dogtown in Rockport and Gloucester, MA featuring varied terrain and named historic trails. Runners and walkers are welcome; early registrants receive T-shirts and prizes are awarded by overall and age categorie..

A trail event in Dunstable, MA supporting the Humane Society for Greater Nashua, featuring a marked 5-mile loop with nearly 600 ft of elevation gain per lap and an optional 6-hour format for repeated laps.

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.

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 timed endurance event on a flat 4 mile rail-trail loop in Poland, Maine; participants may run multiple loops with total mileage recorded and recognized, and paid entries include an event shirt.

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..

Muddy Princess Boston is a women only 5K obstacle mud run at Kimball Farm in Haverhill on June 21, 2026. The course has 18 plus obstacles and is open to women aged 7 and up who may run, jog or walk.

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 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.

Ultratrax Cranmore in North Conway, NH is a single day endurance walk on June 27, 2026 offering 7, 14, 21 and 28 mile loops with a 10 hour cutoff. The course follows forest singletrack and old ski trails with aid stations and timed results.

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.

A community trail festival in East Bayside, Portland on June 28, 2026 featuring a 10K run, 15 or 30 mile bike rides, and a 2 Miler. Registration proceeds support Portland Trails and the Bicycle Coalition of Maine.

A 5K obstacle mud run in Minot, Maine on June 28, 2026 for women and girls aged 7 and older. The course includes 18 plus obstacles and emphasizes a non competitive, teamwork oriented experience.

A family oriented 5k fun run in Tamworth, New Hampshire centered on historic Ordination Rock during July 4 celebrations. Organized by the Tamworth Outing Club, registration includes a bandana, ice cream, and a bib raffle entry.

A backyard ultra on Portlands Back Cove Trail where runners complete about 4.17 mile loops each hour until one runner remains. The mostly flat gravel course runs along a tidal estuary and includes staffed and unstaffed aid stations.

A looped trail 50K at Spaulding Academy in Northfield, NH featuring five 10K technical loops, about 32 miles and 4,000 feet of gain. Ten hour race limit, cupless format, and support for Spaulding Academy & Family Services.

A roughly six-mile uphill trail race to Loon Mountain’s North Peak with about 3,066 ft of climb, very steep sections including the one-kilometer Upper Walking Boss, two fluid stations, and over $20,000 in prize money.