Trail Running calendar near Portland 2025-2026

The ACT Trail Fest, held in Arundel, Maine, is an annual trail running event organized by the Arundel Conservation Trust. Participants can choose from a 5k, 10k, or half marathon course that winds through the scenic ACT Multi-Purpose Trail and Eastern Trails, featuring beautiful woodland and stream..

The Bear Brook Trail Races, held in Allenstown, New Hampshire, showcase the scenic beauty of Bear Brook State Park with its diverse trails, including single track paths, steep hills, and blueberry fields. The event offers three race distances: a 10K following "Mindy's Loop," a Half Marathon, and a M..

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 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 significant elevation gains and technical single-track terrain. Participants tackle a steep 1,700-foot climb up Bald Peak within the first two miles, followed by a descent and another 1,900-foot ascent to t..

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, and a 10k single loop. Each loop features nearly 1,000 f..

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 course features natural terrain with rocks, roots, and possible mud, providing a challenging and imm..

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,..

Big Brad Ultras is an ultramarathon event held in Pownal, Maine, featuring three race distances: a 25K, 50K, and a challenging 50-mile race. The course consists of a rugged 16.5-mile loop through Bradbury Mountain State Park, including trails over Tryon Mountain and around Snowman's loop, with rocky..

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, with courses running along a mix of access roads and ski trails. The route is uniquely marked with reflective flagging and LED lanterns, creati..

The TARC Stone Cat Trail Festival is a renowned trail running event held annually in Ipswich, Massachusetts, within Willowdale State Forest. Offering a variety of distances including 10K, half marathon, marathon, 50-mile, and 100K races, plus a free youth fun run, the festival features a challenging..

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 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 for ch..