Trail Running calendar near Brookline 2025-2026

The Triple Dam 10K is a scenic running and walking event held at the Power Dam Recreation Area in Perkinsville, Vermont. The course is a beautiful loop featuring gently rolling terrain on a mix of grassy trails, dirt roads, and single track, primarily on the west side of the Black River and North Sp..

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..

The Cross-Connecticut Run for Mental Health Awareness is a unique 56-mile group running event held annually in Connecticut, traversing the state north to south along the scenic and flat Farmington Canal Heritage Trail. Starting in West Suffield and ending at New Haven Harbor, the course passes throu..

The Wicked Mudder will take place in Southwick on Sunday 7 September 2025. You can run between 5 and 5 kilometers.

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 Pisgah Mountain Trail Races, held in Pisgah State Park, Chesterfield, New Hampshire, feature two challenging trail distances: a 50K and a 23K. Organized by the Red Clover Rovers, this event supports the New Hampshire Special Olympics, with all profits benefiting their mission. The races start fr..

The Mt. A Trail Challenge is an annual running event taking place at Mount Agamenticus in York, Maine. Scheduled for September 20, 2025, the event features two courses: a 5K and a 1-mile challenge, allowing participants to run, hike, or stroll.The race is timed traditionally with stopwatches, and wh..

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 Hooksett Kiwanis 5K Trail Race is an exciting running event taking place in Hooksett, NH, featuring a 5K race for all runners and walkers, as well as a Kid's Fun Run for children aged 12 and under. The race begins at Heads Pond trail and follows a scenic route through wooded conservation areas,..

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 Vermont 50 Ultra Run is an annual endurance event held at Ascutney Outdoors in West Windsor, Vermont, typically on the last weekend of September. Established in 1993, it features a challenging and scenic course through Vermont's landscape, offering a 50-mile ultra run and a 50K race. The event i..

Run for Nature in Lowell, MA, is a community-focused running event held at Shedd Park, featuring a 10K trail run, a 5K run/walk, and a 1-mile Kids Fun Run/Walk. The course winds through scenic trails in Shedd Park and Rogers Fort Hill Park, including a stretch along the Concord River Greenway, with..

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..

The Aggie Ram Trail Run 5k will take place in Walpole on Sunday 5 October 2025. You can run between 5 and 5 kilometers.

The Houghton's Pond Trail Races feature two distances: a 7-mile race and a 3.7-mile race, set in the scenic DCR Blue Hills Reservation in Milton, MA. Participants will navigate rolling dirt roads and forest paths, with elevation changes of approximately 700 feet for the 7-mile course and 300 feet fo..

The NipMuck Trail Marathon, held in Ashford, Connecticut, is a challenging 26.4-mile trail race along the scenic Nipmuck Trail. The course features diverse terrain including rocks, roots, mud, and wood bridges, with a route that heads south 6.2 miles to Route 44 and back, then north 7 miles to Bosto..

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 Groton Town Forest Trail Races, organized by the Squannacook River Runners and Groton Trails Committee, feature two scenic courses of 9.5 miles and 3.4 miles through the picturesque Groton Town Forest. The trails are well-marked and consist of narrow dirt roads and winding paths, presenting a mi..

The Midstate Massive Ultra Trail is a challenging point-to-point endurance race held in New Ipswich, New Hampshire, traversing the Appalachian Midstate Trail through central Massachusetts and crossing into New Hampshire, Rhode Island, and Connecticut. Scheduled for October 11-12, 2025, it offers thr..

The Ghost Train Trail Races, held in Brookline, New Hampshire, is the state's original 30-hour ultramarathon event along the historic Granite Town Rail Trail. Participants can choose from multiple race options including a 30-hour ultramarathon, a 30-hour 7-person relay, a 30-mile haunted night race,..