Trail Running calendar near Windham 2026-2027

A charity event at Medomak Valley High School with an untimed 1 mile walk, a 5K trail race, and a virtual 5K, with proceeds benefiting Boston Children’s Hospital.

A trail race weekend in Waterville Valley NH with a 50K ultra, 23K, 4 mile and 1 mile family fun run. Courses use single and double track, have cup less aid stations, and include finisher awards and podium prizes.

Two trail races at Five Fields Farm in Bridgton, ME feature technical singletrack and steep climbs, including a three-lap 50K through Bald Pate and Holt Pond preserves and a rugged 10K with significant elevation gain.

A weekly fall trail running and walking series at Great Glen Trails in Gorham, NH from Sep 3 to Oct 8, 2026. Choose from 5 km, 3 km or 1.5 km courses; dogs on leash are welcome and one-time entries are available on-site.

Test your endurance at Pineland Farms in Maine with this backyard ultra trail race. Run a 4.2 mile loop through pristine wooded trails and see how many laps you can complete in this last person standing format.

Experience a flat and non technical trail race at Cherry Hill Farm in Gorham Maine. Choose between 50k 25k or 10k distances consisting of multiple loops around the scenic farm property.

A trail running weekend around Mirror Lake in West Newfield, Maine, with laps of about 3.6 to 3.8 miles through forest roads and singletrack. The weekend includes a Saturday gravel ride, onsite camping, youth runs, and a post ride gathering..

Whites 100 in Shelburne, NH on September 11, 2026 is a non-competitive, fat-ass-style trail event offering five drop bags, bin transport and an online tracker. A refundable $200 bin deposit is required and a 54-hour support cutoff applies.

Trail races in Camden Hills State Park near Penobscot Bay offering 10K, 20K and 50K courses across singletrack and gravel. The festival includes a Wabanaki land acknowledgement and a donation option supporting local Wabanaki food sovereignt..

Trail ultramarathon and half marathon in Bear Brook State Park, Allenstown NH on September 12, 2026. The ultramarathon distance varies year to year and the course is GPX only with minimal course markings.

Thunder Run is a 5K trail race with more than 20 obstacles through woods and hills in Candia, New Hampshire on September 12, 2026. Organized by Raymond Area Rotary, 100% of proceeds support local and selected international projects.

A September mountain race at Echo Lake State Park offering a five mile course and a half marathon that climbs over 4,300 feet of vertical. Courses run on granite ledges and exposed ridges with remote aid stations.

Big Brad Ultras at Bradbury Mountain State Park offers 25K and 50K options on a 15.5-mile single-track loop with technical, hilly terrain, significant elevation gain, aid stations, and drop-bag access.

A community 5K trail run and walk at Skyline Farm on Sunday, September 13, 2026, across fields, hills and woods. The day includes a free kids' 1K fun run, post-event food and music, and prizes for individual and team finishers.

A mountain footrace from the Cog Railway base in Bretton Woods to the summit of Mount Washington, offered as a 2.75 miles climb or a 5.5 miles roundtrip. The route follows the railway, gains about 3,500 feet and crosses steep rocky terrain.

A remote trail event in Stark, New Hampshire with 50 mile, 25 mile and 25K courses along the Kilkenny Ridge Trail. Routes are unmarked, require navigation and mandatory gear, and include backcountry aid stations and shuttle logistics.

Experience the summit of Mount Agamenticus with a 5K or 1 mile trail race. Support local conservation efforts while running or hiking through Maine trails and participate in a raffle for all entrants.

A community 5K trail race in Hooksett that runs from Heads Pond trail through wooded conservation land to the Hooksett Public Library. A separate 0.5 mile kids fun run is available and proceeds support local youth programs.

A 5K trail race at Loon Mountain on September 20, 2026, as part of the 51st NH Highland Games, with 800 ft of elevation gain across dirt trails, service roads and ski trails. Registration includes a race shirt and festival admission.

Pair up for a three hour endurance relay on a two mile loop of trails and fields. Alternate laps with your partner to accumulate the maximum distance possible in this team based challenge.