Trail Running calendar near Kennebunkport 2025-2026

The Last Man Standing Ultramarathon is a backyard ultra event held at Pineland Farms in New Gloucester, Maine. The race features a challenging 4.2-mile loop on wooded trails with moderate elevation gain. Participants must complete each loop within one hour to continue, with laps starting hourly unti..

Black Bear Trail Races, hosted by White Mountain Endurance in Waterville Valley, New Hampshire, offers four distances: a 50K ultramarathon, a 23K, a 4-mile forest trail run, and a 1-mile Bear Cub Fun Run for families. All courses start and finish at Waterville Valley Town Square. The 50K loops aroun..

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 Big Day Brewing Fall Trail Running/Walking Series takes place at Great Glen Trails, with base-lodge facilities and courtyard check-in. Participants may choose from three courses—long 5 km, short 3 km, or mini 1.5 km—with the course varying each fall. Registration is online (free) or in person at..

Cherry Hill Farm Ultra in Gorham, Maine offers two trail options: a 50K and a 25K, run on a flat, fast, non-technical loop around Cherry Hill Farm. The 50K comprises 12 laps of 2.6 miles (31.2 total), while the 25K is six laps. The course threads along the Ecomaine Trail, Burleigh Lovett Trail, Cana..

Set in the Great Brook Farm State Park in Carlisle, Massachusetts, with start/finish at Hart Barn Ski Center, the TARC Fall Classic offers distances of 50 miles, 50K, 20 miles, half marathon, 10K, plus a free youth fun run and the Yeti Mischief Mile. The looped course weaves through woods and fields..

Down for Trail Running is a trail-running weekend in western Maine, held at Mirror Lake in West Newfield. Runners navigate a looping course of forest roads, single-track, rugged sections, and climbs, with each lap roughly 3.6 miles—participants choose how many laps to complete. The course provides a..

Run to Fall 5K is a community cross-country event held at Coe-Brown Northwood Academy on the 1st New Hampshire Turnpike in Northwood, New Hampshire. The program features a 5k cross-country race on the CBNA course, a 2.5-mile trail walk, and youth races on the NH Youth State Meet Course, plus a kids’..

The Happy Moose Half Marathon is a 13.1-mile trail race held in Oxford, Maine, featuring a scenic course through the fields and forests of western Maine. The race consists of three loops of the 4.1-mile Four in the Forest course, plus a separate 0.8-mile loop at the start. This event offers runners..

Four in the Forest is a four-mile trail race held in Oxford, Maine (04270). The course traverses forested areas and open fields in western Maine, offering a scenic, nature-forward experience for trail runners. Runners tackle a predominantly off-road route along Bennett Lane, with a setting that emph..

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..

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..

Bear Brook Trail Races take place at Bear Brook State Park in Allenstown, New Hampshire. The event offers three trail races: Marathon, Half Marathon, and 10K (the 10K follows Mindy’s Loop). The Marathon doubles the Half Marathon route.Runners encounter diverse terrain—from beautiful single-track thr..

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 BLS Wolfpack 5K Cross Country Run or Walk is a 5K event in Boston’s Franklin Park, using the historic Franklin Park cross-country course. It brings together the Boston Latin School community—students, staff, families and alumni—for a morning of running or walking, with the pep band adding energy..

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..

Farm to Farm Ultra is a Maine ultramarathon held in Freeport and Brunswick. The 2025 event includes a 50-mile race, a 50K, a 50K four-person relay, plus 25K and a 25K two-person relay. The course starts at Wolfe’s Neck Farm in Freeport and finishes at Crystal Spring Farm in Brunswick, featuring roll..