Trail Running calendar near Roxbury 2025-2026

The Notchview Ultra is a multi-day ultrarunning event held in Windsor, Massachusetts, featuring a variety of 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 aid sta..

The Second Annual Orange Runners Club Summer Sizzle XC5k is a cross country running event held in Warwick, New York, at the Rich Furst Sanfordville Elementary School XC Course. This 5k race, rooted in teamwork, dedication, competition, and fun, takes place on a course known for its rich cross countr..

The Newbsanity Extreme Ravine Trail Race, held in Binghamton, NY, offers a challenging trail running experience on the southern trail system of the Newbsanity Adventure Center. Participants can choose from a 5K single loop, a 15K race consisting of three loops, or a demanding 12-hour endurance event..

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, held in Esperance, NY, is a scenic cross-country race through the arboretum’s forests and meadows, offering beautiful views of the Schoharie Valley. This rolling 5K course is part of the Route 20 Challenge Series and is USATF sanctioned. The event features chip ti..

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, approximately 15 miles with 5,000 feet of elevation gain and descent, or a shorter 8K course of about 5 miles wi..

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 is a 6-hour ultra running event held at Jug End State Reservation in Egremont, Massachusetts. Participants run multiple laps of a scenic 4.2-mile course featuring woods, fields, and an apple orchard, with an elevation change of 830 feet per lap. The course includes uphill and..

The Thacher Park Trail Running Festival, held annually at Thacher State Park in Voorheesville, NY, offers a scenic and challenging trail running experience. Participants can choose from four distances: 10K, half marathon (13.1 miles), marathon (26.2 miles), and an ultra 50K. The course features a sh..

The Salt Springs Field, Forest & Falls Trail Race, held in Montrose, Pennsylvania, offers a rugged trail running experience through old-growth forests with stunning scenery. In its 13th year in 2025, the event features three distances: 5K, 10K, and a challenging 50K race. The 5K is mostly trail, whi..

The Macedonia Trail Race, held in Macedonia Brook State Park in Kent, Connecticut, offers a unique trail running experience with lush single-track forest trails, challenging climbs and descents, and stunning viewpoints including Cobble Mountain with views of the Catskill Mountains. Now in its 7th ye..

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 70-mile Shawangunk Ridge Trail, which stretches from High Point State Park in New..

The Angevine Farm Trail Festival is a scenic trail running event held in Warren, Connecticut, in the picturesque Northwest corner of the state. The festival features multiple race options including an 8-hour endurance run, a half marathon, and 5K races with a special Canicross category for runners w..

The Gardiner Dump Run is a scenic trail running event held in Gardiner, New York, featuring a 5k race with an option to complete two laps for a 10k distance. The course winds through single-track trails along wooded hillsides near the Wallkill River and untamed fields at Gardiner’s Riverbend Trails,..

The Cat's Tail Trail Marathon is a challenging 26-mile point-to-point trail race held in the Slide Mountain Wilderness Area of the Catskill Mountains, New York. Featuring nearly 7,000 feet of elevation gain, the course offers rugged terrain with rocky, technical climbs and descents, alongside stunni..

The Race to the Face 5k will take place in Norwich on Saturday 27 September 2025.

The Water Gap 50k and 25k is a scenic trail running event held in Milford, Pennsylvania, along the Delaware Water Gap. The race courses follow the McDade Trail, a 32-mile route featuring a mix of rail-trail style cinder paths and singletrack terrain. The trail is non-technical and rolling, making it..