Trail Running calendar near Roxbury 2025-2026

Manitou’s Revenge is a challenging 53-mile ultramarathon held in the Catskill Mountains, starting in Windham, New York. The course follows the northern Black Dome Trail and the Long Path from Acra Point to downtown Phoenicia. Featuring approximately 15,000 feet of elevation gain, the route is rugged..

The Free to Run Trail Races, hosted by the Berkshire Ultra Running Community for Service (BURCS), take place in Pittsfield State Forest, Massachusetts. Scheduled for June 21, 2025, the event offers three distances: 15K, 25K, and 50K ultramarathon. The challenging course features a double-loop figure..

The Red Wing Trail Challenge, held at Red Wing Recreation Area in Lagrangeville, NY, offers two trail race distances: a challenging 60K with approximately 6,600 feet of elevation gain, and a 15K featuring about 1,650 feet of gain. The 60K consists of four laps of a 15K loop that includes varied terr..

The Notchview Ultra, held in Windsor, Massachusetts, is a multi-day ultrarunning event featuring various race durations including 100.7 miles, 72 hours, 48 hours, 24 hours, 12 hours, and 6 hours. The course is a scenic, well-maintained 1.9-mile perimeter loop trail around Notchview, with runners pas..

The Second Annual Orange Runners Club Summer Sizzle XC5k is set to take place at the Rich Furst Sanfordville Elementary School XC Course in Warwick, NY. This exciting event features a 5k run or walk, along with a Kids Dash, promoting teamwork, dedication, and fun in the spirit of cross country runni..

The Newbsanity Extreme Ravine Trail Race is an adventurous running event taking place in Binghamton, NY, featuring a challenging course designed for thrill-seekers. Participants can choose from three events: a 5K, a 15K, or a grueling 12-hour race. The course is set in the southern trail system of t..

The Wakely Dam Ultra is a challenging 55K ultramarathon held in Piseco, New York, within the Adirondack Park wilderness. The race follows a remote, technical trail along the Northville Placid Trail between Piseco Lake and Wakely Dam, featuring 3,300 feet of elevation gain. It is a self-supported eve..

The Landis Arboretum 5K Forest Run is an annual event held in Esperance, NY, showcasing a scenic cross-country course through the Arboretum's forests and meadows. Participants can enjoy stunning views of the Schoharie Valley while competing in this 19th edition of the race. The event features age gr..

The Sweltering Summer Ultra is an annual running event held at Clapp Park in Pittsfield, Massachusetts. The 13th edition features an 8-hour race on a certified 0.355-mile dirt and cinder track, with runners switching directions halfway through. Participants can run or walk as many laps as they choos..

Climb It For Climate is a mountain trail running event held at Belleayre Mountain Ski Center in the Catskill Mountains, New York. Participants can choose between a challenging 25K course featuring approximately 15 miles with 5,000 feet of elevation gain and descent, or a shorter 8K course with 5 mil..

The Fabulous Fahnestock Trail Races, held in Cold Spring, NY, offer runners a choice of 50K, 25K, and 5.5-mile distances through scenic Fahnestock State Park in the Hudson Valley. The course features a mix of runnable dirt roads and technical single-track trails, with challenging climbs, flowy desce..

The Jug End Loop Ultra, held at Jug End State Reservation in Egremont, Massachusetts, is a challenging 6-hour ultra running event featuring a 4.2-mile loop course through woods, fields, and an apple orchard. Each lap includes approximately 830 feet of elevation change, with equal uphill and downhill..

The Thacher Park Trail Running Festival, established in 2014, takes place at Thacher State Park in Voorheesville, NY. This scenic event offers participants a choice of four race distances: 10K, 13.1M, 26.2M, and 50K, allowing runners to experience the park's beautiful trails. The festival promotes a..

The Salt Springs Field, Forest & Falls Trail Race is a challenging and scenic trail running event taking place in Montrose, Pennsylvania. Celebrating its 13th year in 2025, participants can choose from three race distances: 5K, 10K, and 50K. The courses traverse technical trails through an old-growt..

The Macedonia Trail Race, held in Macedonia Brook State Park in Kent, Connecticut, offers trail runners a unique experience with its lush forest trails, challenging climbs and descents, and stunning viewpoints including Cobble Mountain, where runners can see the Catskill Mountains on clear days. Now..

The Brookfield Classic is a trail running event held in the scenic Charles E Baker State Forest in Brookfield, New York. It offers three race distances: a 5K for beginners or casual runners, a family-friendly 15K loop combining truck and horse trails suitable for walking or running, and a challengin..

The Pawling 24 Hour Trail Running Festival, held in Pawling, NY at Lakeside Park, offers runners a challenging and festive endurance experience. Participants can choose from 3, 6, 12 (including a night start), or 24-hour timed races on a 1.68-mile loop course featuring pavement, grass, and single-tr..

The Shawangunk Ridge Trail Run (SRT) is a challenging trail running event held in Rosendale, New York, featuring three race distances: a 70-mile ultra, a 30-mile race, and a half marathon. The course follows the scenic Shawangunk Ridge, a 70-mile trail extending from New Jersey to New York, known fo..

The Gardiner Dump Run is an exciting running event scheduled for September 21, 2025, in Gardiner, NY. Participants can choose between a 5k trail run or a 10k option, which consists of two laps of the 5k course. The race takes place on scenic single-track trails through wooded hillsides near the Wall..

The Angevine Farm Trail Festival, held annually in Warren, Connecticut, offers a scenic and challenging trail running experience in the Northwest corner of the state. The event features multiple distances including a half marathon, a new 8-hour race on a 1.25-mile farm loop, and 5K races including a..