Trail Running calendar near Freeport 2025-2026

The Frye Island Trail Run will take place in Frye Island on Saturday 9 August 2025. You can run 4 miles.

The Jigger Johnson Ultras is a challenging trail running event held in the White Mountain National Forest, Waterville Valley, New Hampshire. It features three race distances: 100 miles, 50 miles, and 20 miles, each traversing rugged, mountainous terrain with significant elevation gains—up to 29,000..

The Maine Event is a challenging seven-day self-guided trail running expedition held in Maine, featuring rugged and scenic routes through iconic landscapes such as Mt. Katahdin, the Bigelow Range, and the Mahoosuc Notch. Participants experience intense daily runs over difficult terrain, with distanc..

The Firebird Trail Races, held in Falmouth, Maine, offer challenging trail running events with distances of 13 miles, a marathon, and a 50K. The courses feature a technical 10-mile loop through Lowell Preserve and North Falmouth Community Forest, with additional loops in East Windham Conservation Ar..

The Last Man Standing Ultramarathon will take place in New Gloucester on Saturday 30 August 2025. You can run 4 miles.

The Black Bear Trail Races, hosted by White Mountain Endurance, take place in scenic Waterville Valley, New Hampshire. This trail running event offers multiple distances: a challenging 50K ultra with 7,700 feet of elevation gain around iconic 4,000-foot peaks, a classic 23K course through the oldest..

The Five Fields Farm Races, held in Bridgton, Maine, feature two challenging trail events: a 50K ultra and a 10K race. The 50K is a three-lap figure-8 course through the Bald Pate and Holt Pond Preserves, including steep climbs, technical singletrack, and a finish through an apple orchard. Each lap..

The Megunticook Trail Festival in Camden, Maine, offers three challenging trail races set in the scenic Camden Hills State Park where mountains meet the sea. The events include a grueling 50K ultramarathon with over 7,600 feet of elevation gain, traversing 90% of the park's trails and summiting six..

The Cherry Hill Farm Ultra, held in Gorham, Maine, is a trail running event featuring 50K, 25K, and 10K distances. The main 50K race consists of 12 flat, non-technical loops of 2.6 miles each around Cherry Hill Farm, totaling 31.2 miles. A 25K option includes 6 loops.The course is designed to challe..

Down for Trail Running is a community-focused trail running event held in West Newfield, Maine, set against the scenic backdrop of Mirror Lake. Participants can choose multiple laps on a course featuring a mix of double track forest roads, rugged single-track sections, and climbs, emphasizing the ex..

The Run to Fall 5K is an annual cross-country race held at Coe-Brown Northwood Academy in Northwood, New Hampshire. Celebrating its 25th edition in 2025, the event features a 5K cross-country race, a 2.5-mile trail walk, and youth USATF 3K races for different age groups. A kids' fun run around the t..

The Four in The Forest will take place in Oxford on Saturday 13 September 2025. You can run 4 miles.

The Happy Moose Half Marathon will take place in Oxford on Saturday 13 September 2025. You can run 13 miles.

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 Gunstock 5K and Canicross 5K take place at Gunstock Mountain Resort in Gilford, NH, as part of the annual Food Truck Festival. The event features a 5K trail run and a Canicross 5K where participants run with their dogs, followed by a 100m fun run for children under five. The course is a loop aro..

The ACT Trail Fest, held in Arundel, Maine, is an annual trail running event featuring 5k, 10k, and half marathon distances. Participants run or walk through the scenic Arundel Community Trails and Eastern Trail, enjoying woodland and stream views. The race starts and finishes at the Arundel Municip..

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 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..