Trail Running calendar near Kennebunkport 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 Webb Forest Wander is a family-friendly 5K race held in the scenic Webb Forest trail system in Wilmot, New Hampshire. Organized by the Wilmot Learning Place, a nonprofit preschool, the event offers a well-marked course through a beautiful nature preserve maintained by the New London Conservation..

The GTA Challenge is a 10K trail race held in Greenfield, New Hampshire, organized by the Greenfield Trail Association to support local trail maintenance. The course features a mix of class 6 roads, double track, and single track trails with natural obstacles like rocks and roots, offering a challen..

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..

Greenbelt's Vineyard Hill Trail Run is an annual trail running event held in South Hamilton, Massachusetts, located on the scenic town line of Hamilton and Topsfield. The race offers 5K and 10K distances that traverse Vineyard Hill, sections of Bradley Palmer State Park, the Bay Circuit Trail, and G..

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 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..

The TARC Fall Classic is a popular trail running event held at Great Brook Farm State Park in Carlisle, Massachusetts, offering a range of distances including 10K, half marathon, 20 mile, 50K, and 50 mile races, plus a Yeti Mischief Mile and a free youth fun run. The courses wind through scenic New..

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 Veterans Count Nashua 5k Fun Run & Walk will take place in Nashua on Sunday 14 September 2025. You can run between 5 and 5 kilometers.

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 Hooksett Kiwanis 5K Trail Race, held in Hooksett, New Hampshire, is a scenic trail run starting at Heads Pond trail and finishing at the Hooksett Public Library. The course features a hard-packed stone dust surface and wooded conservation trails, offering a natural and enjoyable running experien..