Trail Running calendar near Woodbury 2026-2027

A point-to-point, rugged trail marathon with nearly 7000 feet of elevation gain in New York's Catskill Mountains. The route features technical climbs, scenic views, and multiple aid stations, with proceeds supporting land conservation.

Run the scenic McDade Trail through the historic Delaware Water Gap. The non-technical, rolling course is a mix of cinder path and singletrack. Each entry includes a finisher's item and supports trail maintenance.

The Front Runners New York Cross Country 5K will take place in Bronx County on Saturday 26 September 2026. You can run 5 kilometers.

The Gardiner Dump Run offers 5k and 10k trail races through the scenic Riverbend Trails. The course winds along wooded hillsides and fields near the Wallkill River. Day-of registration is available, and the event features a sneaker recyclin..

IronHike Endurance Series runs October 1 to October 4, 2026 at Mohawk Mountain Ski Area in Cornwall CT. The series offers multiple ultra trail events from about 61 miles to 152 miles with large elevation gains and run, hike or walk options.

This 24-hour trail challenge in Cornwall, CT, covers over 28 miles and 13,685 feet of elevation gain. Participants can run, hike, or walk the double marathon distance or tackle it as a relay.

Event Overview The Tesla Hertz Run is a multi-distance trail running event held in Rocky Point, New York, on Long Island. The races take place over a weekend in early October. Participants can choose from several distances, with specific st..

Challenge your legs on the slopes of Mohawk Mountain Ski Resort in Cornwall, CT. Choose from marathon, half marathon, 10K, or 5K distances on a course featuring climbs, descents, and fall foliage views. Hikers are welcome on the shorter tra..

A single-loop half marathon through five parks in lower Westchester County, New York, starting at the Thomas Paine Cottage and finishing at New Rochelle High School. Mostly shaded dirt trails with varied wildlife and published race results.

The NSRF Great Pumpkin Dash Trail 5K will take place in Smithtown on Sunday 11 October 2026. You can run 5 kilometers.

Experience Long Island scenery at the Suffolk County Marathon in Bay Shore. Choose from distances ranging from a 1k kids run to a full marathon, all while supporting local veterans.

This 3.5-mile trail run/walk on the flat Mill Pond Trail happens in Wolcott, CT. The Wolcott Lions Club hosts the event, which includes a race t-shirt and clam chowder. Registration opens online with a lower early-bird rate.

Tackle the technical trails of Harriman State Park at the Big Bear SquaTCh South. Choose a challenging half marathon or 10K on a scenic loop with significant elevation gain. Your registration supports local trail maintenance, and the event..

This Halloween-themed run on New Jersey's legendary Clinton Road offers a spooky adventure. Participants can choose from a Zombie Crawl, a 5k, or a 10k, all featuring zombie volunteers and a festive finish line celebration.

A 5 mile trail race at Muscoot Farm in Katonah, NY on October 25, 2026, with two kids races for specified age groups. Participants receive Farm Bucks for the farmers market; shirts are optional and ordered in advance.

The Fall Back Into The Trails Series returns to New York's Red Wing Recreation Area. Runners can tackle a 100k, 50k, or 10k on challenging, looped courses. All finishers earn a custom medal, and the ultras are UTMB Index races.

This 8-hour timed trail run takes place on the rolling farm trails at Gurski Farm in Brookfield, CT. Runners complete as many laps as possible on a course featuring single track. It offers a community atmosphere where participants frequentl..

Test the reverse direction of the 5-mile loop at Jacobsburg State Park. Choose from a single loop, a 3-hour, or a 6-hour timed event on mixed trails. It's a hiker-friendly, cupless event focused on sustainability.

Run through the historic carriage roads of the Rockefeller State Preserve in the Hudson Valley. The single-loop marathon and half marathon courses pass fields, stone walls, and scenic vistas without any pavement or cars. It's a walk-friendl..

Celebrate the tenth anniversary of this event with an 8K or 5K trail run through Unionville Vineyards. Enjoy live music and a glass of wine at the post race reception in Ringoes.