Trail Running calendar near Roxbury 2025-2026

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 Front Runners New York Cross Country 5K is an exciting running and walking event scheduled to take place at Van Cortlandt Park in the Bronx on September 27, 2025. This event invites participants of all skill levels to enjoy a scenic course while promoting fitness and community spirit. The 5K run..

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..

The IronHike Endurance Series, held at Mohawk Mountain Ski Area in Cornwall, Connecticut, is a multi-day endurance event featuring rugged, scenic courses designed to challenge participants with significant elevation gains. Spanning from October 2 to 5, 2025, the series offers various timed events ra..

The NJ Trail Series One Day is a multi-day ultrarunning event held at the Sussex County Fairgrounds in Augusta, New Jersey. Taking place from October 2 to 5, 2025, it offers a variety of race options including 72, 48, 24, 12, and 6-hour timed races, as well as marathons and 50K distances. The course..

The Run for the Pumpkins Trail Run, held in Westerly, Rhode Island at Bradford Preserve, is part of the WTAC Fall Race Series. This event features 5K and 10K trail races, along with a free 1K children's run for ages 10 and under. The courses highlight preserved town land and the Woody Hill Managemen..

The Run the Vineyards - Pindar Fall 5K and 8K is a scenic autumn race held at Pindar Vineyards in Peconic, NY, featuring courses through 300 acres of vineyard property. Participants can choose between a 5K or 8K race on a mostly flat course consisting of hard-packed dirt trails and short-cut grass,..

The KMT Fall Foliage Frenzy is a timed trail running event held in Montebello, NY, near Kakiat Park and Harriman State Park. Participants can choose between 3-hour and 6-hour race options, running on a challenging 2.33-mile loop with approximately 660 feet of vertical gain. The course offers stunnin..

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..

The Norfolk Land Trust Trail Race Series, including the Haystack Mountain Challenge, is held annually in Norfolk, Connecticut. The event features three trail races: a 5K, 10K, and a challenging half marathon. The 5K course runs through scenic Barbour Woods with a mix of single and double track trail..

The Tesla Hertz Run, held in Rocky Point, NY, is a multi-distance ultramarathon event featuring races from 10 miles up to 150 miles. The course is a scenic 10.48-mile loop through the pine barrens of Long Island, offering a remote trail experience with minimal outside interaction. Runners benefit fr..

The Forbidden Forest 30 Hour Ultra Run is an epic endurance event held in Stratford, Connecticut, offering runners up to 30 hours to complete distances ranging from a marathon (26.2 miles) to 100 miles or more. The course features a challenging 2.23-mile loop with roots, rocky terrain, and a notable..

The Mohawk Mountain Race, held at Mohawk Mountain Ski Area in Cornwall, Connecticut, offers a challenging trail running experience with marathon, half marathon, 10K, and 5K distances. The course features steep ascents and descents on ski mountain trails, including the Wildwood, Timber, Pine, Laurel,..

The Paine to Pain Trail Half-Marathon is a distinctive trail race held in Westchester County, New York, starting at the historic Thomas Paine Cottage in New Rochelle and finishing at New Rochelle High School. This 13.1-mile single-loop course traverses the woods and trails of five different parks, o..

The 2025 Never Stop Running Foundation Great Pumpkin Dash Trail 5K is a scenic trail run/walk held at Blydenburgh County Park in Smithtown, NY. The course features shaded trails with a mix of dirt roads and hard-packed surfaces, suitable for first-time trail runners, though strollers and wagons are..

The Mt. Tom Trail Race, held in Massachusetts' Mt. Tom State Park, offers runners a challenging experience amid stunning fall foliage.Participants can choose from a solo 25k race with 3,600 feet of elevation gain, a 2-person 25k relay, or a solo 10k. The course features rugged single-track trails wi..

The Tackle the Trail - Pomfret, CT will take place in Pomfret on Saturday 18 October 2025. You can run between 10 and 26 miles.

The Castle to River Run in Garrison, NY, is a scenic running event held in the historic Hudson Valley, featuring a half marathon and a 5K race, along with a kids fun run. The half marathon course winds through Hudson Highlands State Park, passing the historic Osborn Castle and offering a mix of sing..

The FALL Run The Farm is a 5-mile trail race held at Muscoot Farm in Katonah, NY, scheduled for October 19, 2025. The event features a main 5-mile race open to ages 6 to 108, along with two kids' races: one for ages 7-12 and another for children 6 and under. The race showcases the scenic beauty of M..

The Big Bear Squatchtoberfest, hosted by Sassquad Trail Running and the New York-New Jersey Trail Conference, is a challenging trail running event held at Harriman State Park in Tuxedo, New York. Scheduled for October 19, 2025, it features a half marathon and a 10K race on rugged, technical trails w..