Trail Running calendar near Jackson 2025-2026

The Kismet Cliff Run, held annually in September in North Conway, New Hampshire, offers two challenging trail races set in the scenic White Mountains. Participants can choose the Little Beast 5 Miler, featuring technical single-track trails with steep ascents and descents around Echo Lake State Park..

The Mt. A Trail Challenge is an annual running event taking place at Mount Agamenticus in York, Maine. Scheduled for September 20, 2025, the event features two courses: a 5K and a 1-mile challenge, allowing participants to run, hike, or stroll.The race is timed traditionally with stopwatches, and wh..

The 2025 ACT Trail Fest, held at 257 Limerick Road in Arundel, Maine, offers a scenic trail running experience through the Arundel Conservation Trust's multi-purpose trails and the Eastern Trail. Participants can choose from a 5K, 10K, or half marathon, all starting and finishing at the Arundel Muni..

The Hooksett Kiwanis 5K Trail Race is an exciting running event taking place in Hooksett, NH, featuring a 5K race for all runners and walkers, as well as a Kid's Fun Run for children aged 12 and under. The race begins at Heads Pond trail and follows a scenic route through wooded conservation areas,..

The Bear Brook Trail Races, set in the scenic Bear Brook State Park in Allenstown, NH, offers participants a choice of three challenging races: a 10K, Half Marathon, and Marathon. The event showcases beautiful trails, including single tracks and steep hills, with a focus on minimizing litter by requ..

The Kilkenny Ridge Race is a challenging trail running event held in Stark, New Hampshire, featuring 50-mile, 25-mile, and 25K distances. The course follows the Kilkenny Ridge Trail through the White Mountain National Forest, including ascents of Mount Cabot and Mount Waumbek, with approximately 7,5..

The Royal (multi) Mile Hill Run is a challenging 5K race held during the NH Highland Games & Festival in Lincoln, New Hampshire. Scheduled for September 21, 2025, the event features a course with an elevation gain of 800 feet, traversing dirt trails, service roads, and ski trails. Participants recei..

The Westmore Mountain Challenge is a one-day, 26-mile trail running and hiking event in Vermont's Northeast Kingdom, featuring five mountains: Moose, Hor, Pisgah, Haystack, and Bald. Participants traverse steep, scenic trails with significant elevation gains, including a marathon option that extends..

The Farm to Farm Ultra is a running event scheduled for September 28, 2025, in Freeport, Maine. It offers multiple race distances, including a 50-mile, 50K, 25K, and relay options. The course features scenic rolling hills on paved roads and trail sections through Crystal Spring Farm, with aid statio..

The Pleasant Mountain Race, held in Bridgton, Maine, is a challenging 21k trail run featuring significant elevation gains and technical single-track terrain. Participants tackle steep climbs, including 1,700 feet over 2 miles up Bald Peak and another 1,900 feet over 2.5 miles on the Southwest Ridge..

The Bobcat Ridge 25k is a trail race set in the scenic Edwin L. Smith Preserve in Kennebunkport, Maine. This 25k event aims to promote outdoor activity while benefiting the Kennebunkport Conservation Trust.Registration is limited to 100 participants, with a deadline for shirt-included registration o..

Bubba's Backyard Ultra is an exciting running event held in Center Conway, NH, featuring the Last Person Standing format. Participants tackle a challenging 3.5-mile loop course that includes forest trails, snowmobile paths, fields, and logging roads, with an elevation gain of approximately 250 feet..

Trust Trail Fest October is a trail running event held at the Kennebunkport Conservation Trust headquarters in Kennebunkport, Maine. Participants can choose between a 5k or 10k race that winds through scenic forest trails featuring natural terrain such as rocks, roots, and occasional mud. The course..

The Devil's Den Ultra is an exciting running event taking place in Bradford, Vermont, featuring a challenging 6.4-mile loop course on Wright's Mountain. Participants can choose from three race lengths: a 30-hour, a 12-hour, or a 6-mile race. The course offers a mix of terrain, including steep climbs..

The Land of Light 100k is a unique running and cycling event taking place in Norway, Maine, featuring a challenging course that combines 25 kilometers of running and 75 kilometers of cycling across six different trail systems. Participants can compete solo or in relay teams, with transitions allowed..

The Trapp Lodge Mountain Marathon is a challenging trail running event held at the scenic Trapp Family Lodge in Stowe, Vermont, nestled in the Green Mountains. Offering both half and full marathon distances, the race features a 13.1-mile loop with approximately 2/3 double track and dirt roads, and 1..

The Randolph Ramble is a challenging 10-kilometer trail race set in the scenic Great North Woods of Randolph, New Hampshire, located at the base of the Northern Presidentials. This self-supported race emphasizes participants' self-sufficiency, as there are no aid stations along the course. Runners a..

The Big Brad Ultras is a challenging trail running event held in Pownal, Maine, featuring multiple race distances: 50 Miler, 50K, and 25K. Participants will navigate a scenic 16.5-mile loop through Bradbury Mountain State Park, including rugged terrain with hills, rocks, roots, and scenic vistas, es..

The Blackout 5k/10k is a mountain race held at Cranmore Resort in North Conway, NH, on November 1, 2025. Participants can choose between a 5K or 10K course, which features a mix of access roads and ski trails, illuminated with reflective flagging and LED lanterns. The event includes check-in, bib pi..

The Jackson 5k Turkey Trot & Kids Fun Run is a Thanksgiving morning event held in Jackson, New Hampshire. The race features a 5k trail run through scenic areas including the Jackson Nordic Trails and Eagle Mountain House golf course, starting at Jackson Falls Bridge. There is also a 1k Kids Fun Run..