Trail Running calendar near Jackson 2025-2026

The Bear Brook Trail Races take place in Bear Brook State Park, Allenstown, New Hampshire, offering a marathon, half marathon, and 10K race. The courses feature scenic single-track trails, steep climbs, and expansive blueberry fields, showcasing the park's natural beauty. The marathon consists of ru..

The Mt. A Trail Challenge is an annual running event held at the summit of Mount Agamenticus in York, Maine. The 9th edition features two courses: a 5K and a 1 Mile trail run, hike, or stroll.The race is uniquely timed with stopwatches by the local York High School Cross Country Team, emphasizing a..

The Royal (multi) Mile Hill Run is a 5K trail race held in Lincoln, New Hampshire, as part of the 50th Annual NH Highland Games & Festival. The challenging course features 800 feet of elevation gain across dirt trails, service roads, and ski trails at Loon Mountain. Participants receive a race shirt..

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 rugged public trails with a cumulative elevation gain of about 6,142 feet, enjoying spectacular..

The Farm to Farm Ultra is a scenic ultramarathon held in Freeport and Brunswick, Maine, featuring distances of 25K, 50K, and 50 miles, along with relay options. The course primarily follows paved roads with rolling hills and includes about two miles of runnable trail per 25K loop, connecting Wolfe's..

The Pleasant Mountain Race, held in Bridgton, Maine, is a challenging 21k trail run featuring technical single-track paths and scenic views along Pleasant Mountain’s iconic ridge. The course includes significant elevation gains, with a steep 1700-foot climb over 2 miles up Bald Peak, followed by a 1..

The Moxie's Memorial will take place in Oxford on Sunday 28 September 2025. You can run 5 kilometers.

The Bobcat Ridge 25k is a trail running event held at the Edwin L. Smith Preserve in Kennebunkport, Maine. This 25-kilometer race takes participants through scenic trails within the preserve, offering a challenging and beautiful outdoor experience.The event supports the Kennebunkport Conservation Tr..

Bubba's Backyard Ultra, held in Center Conway, New Hampshire, is a unique endurance running event featuring the Last Person Standing format. Participants run a 3.5-mile loop primarily on forest singletrack, with some snowmobile trails, fields, and logging roads, including about 250 feet of elevation..

The Little Duck 50k is a trail running event held in Windham, Maine, at the scenic East Windham Conservation Area. Scheduled for October 5, 2025, it offers two race distances: a challenging 50k ultra-marathon consisting of five 6.5-mile loops with nearly 1,000 feet of elevation gain per loop, and a..

Trust Trail Fest, held at the Kennebunkport Conservation Trust headquarters in Kennebunkport, Maine, offers participants a choice between a 5k walk/run and a 10k run through scenic forest trails. The courses feature natural terrain with rocks, roots, and possible mud, providing a challenging and imm..

Devil's Den Ultra is a challenging trail running event held in Bradford, Vermont, featuring a rugged 10K loop on Wright's Mountain. The course offers a mix of terrain, including steep climbs, rocky and rooty sections, and a scenic downhill through the woods. Runners can choose from three race option..

The Vulcan's Fury Trail Race, held in Nottingham, New Hampshire, offers a challenging and scenic trail running experience inspired by the area's volcanic history. Participants can choose between a half marathon and a 5-mile race, both featuring rugged terrain including massive boulder fields, dense..

The Land of Light 100k is a unique human-powered race held in Norway, Maine, featuring a combination of running and cycling across six distinct trail systems. The event covers a total of 100 kilometers, with 25k of running and 75k of cycling, starting at Virgil Parris Preserve. Participants navigate..

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 a mix of smooth, runnable trails, rugged single trac..

The Randolph Ramble is a challenging 10-kilometer trail race held in the mountain town of Randolph, New Hampshire, nestled in the Great North Woods at the base of the Northern Presidentials. Known for its rugged terrain, the race emphasizes self-sufficiency, with no aid stations along the course and..

The Thorne Head Trail Run is a community-focused 4k trail race held at Thorne Head Preserve in Bath, Maine. Hosted by the Kennebec Estuary Land Trust, this event features a mix of fun single-track and wider trails with scenic water views. Designed to be inclusive for both first-time trail runners an..

The Big Brad Ultras, held in Pownal, Maine, offers challenging trail races featuring a 16.5-mile loop through Bradbury Mountain State Park, including Tryon Mountain and Snowman's loop. The course is rugged with hills, rocks, roots, and minimal flat terrain, plus a short stretch of paved and dirt roa..

The Blackout 5k/10k is an exciting mountain race held at Cranmore Resort in North Conway, New Hampshire. This nighttime event features 5K and 10K distances run on a course combining access roads and ski trails, marked with reflective flagging and LED lanterns to guide participants. Headlamps are man..

The Holistic Hustle 5K/10K is an annual running event held at the scenic Emmons Preserve in Kennebunkport, Maine. The 4th edition, scheduled for November 1, 2025, features timed 5K and 10K run/walk races alongside a kids' half-mile fun run for participants aged 13 and under. The event offers a livel..