Trail Running calendar near Tuxedo Park 2025-2026

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

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

The MuleSkinner Endurance Races take place in Upper Black Eddy, Pennsylvania, featuring distances of 50 miles, 50K, marathon, and half marathon. The course primarily follows the scenic, non-technical towpaths along the Pennsylvania side of the Delaware River, offering beautiful views and an easy tra..

The Tom Centinaro Memorial "Dam" Race will take place in Waterbury on Saturday 18 October 2025. You can run 3 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..

Run The Farm in Katonah, NY, is a scenic 5-mile trail race held at Muscoot Farm, showcasing the natural beauty of the area. The event includes a main 5-mile race for ages 6 to 108, plus two kids' races: one for ages 7-12 and another for children 6 and under. Participants receive "Farm Bucks" to spen..

The Big Bear Squatchtoberfest is a challenging trail running event held at Harriman State Park in Tuxedo, New York. Organized by Sassquad Trail Running in partnership with the New York-New Jersey Trail Conference, it features a half marathon (13.1 miles) and a 10K race. The courses are technical wit..

The 3rd Annual Chesterfield FALL Terrain 5K is a community-focused running event held at Fenton Lane Park in Chesterfield, NJ. Scheduled for October 19, 2025, the race features a USATF-certified 5K course combining gravel, trail, grass, and road surfaces, offering a varied terrain experience. The ev..

The Hot Chili Challenge is a trail running event held in Andover, New Jersey, featuring an 8-mile trail run, a 5K run for adults, and a Kids Fun Run for ages 5-12. Participants in the adult races receive t-shirts, hobo bags, and finisher medals, while kids receive finisher medals. Awards and swag ar..

The Bimblers Bluff 50K is an off-road trail race held in southern Connecticut, starting at Guilford Lakes School. The course traverses several interconnected woodland preserves, featuring rolling forest roads and single-track trails that can be extremely rocky. Unlike many ultras, the route does not..

The WXT Ultra is a trail running event held in Titusville, New Jersey, starting and finishing at Washington Crossing Park. It offers two distances: a 25K and a 50K. The 25K course features mostly single-track trails, including an 8.5-mile section within the park and short road segments.The 50K begin..

The Fall Back Into The Trails Series, held at Red Wing Recreation Area in Lagrangeville, NY, offers challenging trail races including a 100K, 50K, and 10K. The 50K consists of five 10K loops with approximately 5,000 feet of elevation gain, while the 100K features ten 10K loops with about 1,000 feet..

The Long Run - Fall Back is a trail running event held at Jacobsburg State Park in Wind Gap, Pennsylvania. Participants can choose from a 5-mile loop, a 3-hour, or a 6-hour timed event, running a course featuring approximately 450 feet of elevation change on a mix of single track and gravel trails...

8 Hours at the Farm is a trail running event held at Gurski Farm/Williams Park in Brookfield, Connecticut. The race features a rolling country course with an approximately 4-mile loop that includes single track and farm trails, offering a scenic and community-focused atmosphere. Participants can cho..

The Pocantico Hills Marathon, held in Sleepy Hollow, NY, offers both marathon and half marathon distances through Rockefeller State Park. The single-loop courses feature rolling hills with scenic views of the Hudson River and Palisades, passing fields, stone walls, bridges, lakes, streams, forests,..

The Raven Rocks 10k Trail Run is an annual challenging trail race held at Ward Pound Ridge Reservation in Cross River, NY. The course features rugged terrain with rocky climbs, ridgeline trails, hilly meadows, and ravines, ascending to the park's two highest points: Raven Rocks Overlook and the Fire..

The NSRF Long Island Turkey Trail Trot 5K is an annual family-friendly run/walk held at Bethpage State Park in Bethpage, NY. The course starts on a grassy polo field and winds through scenic, mostly flat, beginner-friendly trails with a true cross-country feel. Participants enjoy post-race refreshme..

NYC Trail Mix is an annual ultra trail running event held in Staten Island, New York, featuring distances of 50 miles, 50K, and a half marathon. The course showcases over 35 miles of trails through the greenest parts of New York City, including Blood Root Valley, High Rock Park, La Tourette Park, an..

The Tarrywile Half Marathon, held at Tarrywile Park in Danbury, Connecticut, is a challenging trail race known for its significant elevation gain of nearly 3,000 feet and technical Northeast single-track terrain. The course offers stunning views of Danbury and the park's tranquil lakes. The event fe..

The Fall Fling will take place in Southington on Saturday 22 November 2025. You can run between 4 and 6 kilometers.