Trail Running calendar near Kennebunkport 2026-2027

Experience a scenic New England trail event in Dunstable with a 5 mile loop or a 6 hour timed challenge. Support the Humane Society while running through historic quarries and former ski hills.

Experience a unique mountain race alongside the historic Cog Railway to the summit of Mount Washington. Choose between a steep 2.75 mile climb or a technical 5.5 mile round trip through the rugged Presidential Range.

Six at the Springs is a flexible six-hour endurance run in Poland, Maine. Participants run a scenic 4-mile flat loop as many times as they wish, with multiple morning start times. All mileage is recognized, and the event highlights local tr..

Run a scenic yet rugged half marathon trail race at Lynn Woods Reservation in Massachusetts. This 13.1-mile event features three challenging loops showcasing the historic Stone Tower. The focus is on sustainability and a centralized start/f..

UltraTrax Cranmore is a summer endurance walk in the White Mountains featuring 7 to 28 mile options on a scenic 1,775 foot elevation loop. Participants can walk, hike, or ruck with added weight to earn finisher patches and medals.

Enjoy a community celebration in Portland with a 10k trail race, scenic bike rides, or a family friendly 2 mile walk. Finish the day with a festival featuring food trucks, music, and local beer to support Maine trails.

Kick off Tamworth Family Day with this scenic 5k on July 4th. The point-to-point course tours the village and trails, finishing with ice cream and a bib raffle. It's a local tradition celebrating community arts and culture.

The Spaulding Woods 50K is a technical trail race on a 5.6-mile loop in Northfield, New Hampshire. Runners complete six laps, with 4,400 feet of elevation gain, within a ten-hour limit. The event supports Spaulding Academy & Family Services..

Experience a focused fell race on the Isle of Man featuring a 4.5 km course with 150 meters of elevation. This Summer Hill league counter event starts from the Ardwhallan Outdoor Pursuit Centre.

Experience technical trail running in New Hampshire with two demanding distances over the Baldfaces and Mount Meader. This event features steep ledges and panoramic views within the scenic White Mountain National Forest.

The Kingman Farm Trail Race is an old-school, show up and race event over 3.8 miles of rolling nordic paths and switchback singletrack. It benefits the Doug Flutie, Jr. Foundation for Autism. Day-of registration is available.

About the Event The Scribners Mill 5k is part of the Loon Echo Trail Race Series. All proceeds from the series benefit the Loon Echo Land Trust, a Bridgton-based nonprofit that conserves land, protects public access to the outdoors, and bui..

The Ragged 75 offers a rugged three-day stage race and a demanding 50k on the scenic SRKG Greenway trails in New Hampshire. Runners summit multiple peaks over technical terrain, with overnight camping and a communal atmosphere. The event ma..

The 5K Race to the Ledges will take place in Concord on Saturday 8 August 2026. You can run 5 kilometers.

Test your endurance in the White Mountains of New Hampshire with distances ranging from 20 to 100 miles. Navigate technical trails and significant elevation gains in this rugged mountain event starting from Waterville Valley.

The Firebird Trail Races in Windham, Maine offer rugged trail running on a technical loop through the Lowell Preserve. Choose from a 13-mile, marathon, or 50K distance on a course marked by rocks and roots. This grassroots event supports lo..

The annual Vineyard Hill Trail Run features a scenic 5K/10K course over Vineyard Hill and through Bradley Palmer State Park. It's part of the North Shore Trail Series and includes a fully marked trail with an aid station.

Join the Black Bear Trail Races in New Hampshire's scenic Waterville Valley. Choose from four trail distances, including a 50K with major mountain climbs. All runners receive a finisher's medal and finish near the Town Square.

The Five Fields Farm Races offer a scenic 50K and a challenging 10K on the trails of Maine's Bald Pate and Holt Pond Preserves. Both courses start and finish at the farm's apple orchard. All event proceeds support local land conservation.

Join the Trail Animals Fall Classic at Great Brook Farm for scenic trails and distances from youth fun runs to 50 mile ultras. Community vibe, limited spots, and on course aid make this a favorite, so bring your own hydration and register e..