Trail Running calendar near Freeport 2025-2026

The ACT Trail Fest, held in Arundel, Maine, is an annual trail running event featuring 5k, 10k, and half marathon distances. Set on the scenic Arundel Community Trails and Eastern Trail, the courses offer beautiful woodland and stream views. The race starts and finishes at the Arundel Municipal Buil..

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 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 consists mainly of rolling hills on paved roads with about 2 miles of runnable trail per 25K loop, connecting Wolfe's Neck Farm..

The Pleasant Mountain Race, held in Bridgton, Maine, is a challenging 21k trail run featuring technical single-track trails 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..

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 through mostly forest singletrack, with some snowmobile trails, fields, and logging roads, including about 250 feet of elevati..

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 occasional mud, providing a challenging and i..

The Land of Light 100k is a unique endurance event held in Norway, Maine, featuring a combination of running and cycling across six distinct trail systems. The race covers a total of 100 kilometers, with 25k of running and 75k of cycling, all human-powered without the use of cars between segments. S..

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 Thorne Head Trail Run, hosted by the Kennebec Estuary Land Trust in Bath, Maine, is a community-focused 4k (2.5 miles) trail race set in the scenic Thorne Head Preserve. The course features a mix of fun single-track and wide trails with riverfront views of the Kennebec River and Whiskeag Creek,..

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 is an annual running event held at the scenic Emmons Preserve in Kennebunkport, Maine. The 4th edition features timed 5K and 10K run/walk races, along with a kids' half-mile fun run. Participants receive unique wood-burned finisher medals, and top male and female finishers in the..

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