Trail Running calendar near Rocky Point 2025-2026

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 IronHike Endurance Series is a unique multi-day event taking place at Mohawk Mountain in Cornwall, CT, from October 2 to October 5, 2025. Participants can choose from various challenges, including individual and team formats, with distances ranging from 15 to over 152 miles, featuring significan..

The Run for the Pumpkins Trail Run is part of the WTAC Fall Race Series, taking place at Bradford Preserve in Westerly, Rhode Island. Scheduled for October 4, 2025, the event features a 10K, a 5K, and a children's 1K run for participants aged 10 and under. The courses showcase the natural beauty of..

The NipMuck Trail Marathon is a challenging 26.4-mile race held on the scenic Nipmuck Trail in Ashford, Connecticut. Participants can choose between the full marathon or a relay option, where two runners share the distance. The course features a mix of terrain, including rocks, roots, and mud, makin..

The Run the Vineyards - Pindar Fall 8K is a scenic running event set in the picturesque Pindar Vineyards in Peconic, NY. Participants can choose between an 8K and a 5K race, both featuring flat courses primarily on hard-packed dirt trails and grass, making them walker-friendly. The event includes ch..

The KMT Fall Foliage Frenzy is a trail running event held in Montebello, NY, featuring 3-hour and 6-hour timed races. Participants run on a scenic 2.33-mile loop with approximately 660 feet of vertical gain, offering stunning views of the changing leaves in Kakiat Park near Harriman State Park. The..

The Tesla Hertz Run is an exciting running event taking place in Rocky Point, NY, featuring various race distances including a 150 Miler, 100 Miler, 100K, 50 Miler, 50K, and 10 Miler. Set in a picturesque area of Long Island, the course offers a scenic 10.48-mile loop through the pine barrens, provi..

The Forbidden Forest 30 Hour Ultra Run is an exciting endurance event set in Stratford, CT, where participants can run, power-hike, or walk for up to 30 hours. This ultra run offers various distance options, including 26.2M, 50K, 50M, 100K, and 100 miles, allowing runners to challenge themselves at..

The Mohawk Mountain Race, organized by Steep Endurance, takes place at the Mohawk Mountain Ski Area in Cornwall, CT. This unique event transforms the ski mountain into a challenging running course featuring 5K, 10K, Half Marathon, and Marathon options. Participants will navigate steep ascents and de..

The Paine to Pain Trail Half Marathon is a scenic race set in Westchester County, New York, featuring a unique course that traverses the woods and trails of five different parks. This challenging half marathon offers participants a chance to experience nature while running predominantly on dirt trai..

Big Bear Squatchtoberfest is a trail running event hosted by Sassquad Trail Running and the New York-New Jersey Trail Conference, taking place at Harriman State Park in Tuxedo, New York. Participants can choose between a challenging half marathon and a 10K, both featuring rugged terrain, steep climb..

Run The Farm is a trail running event scheduled for October 19, 2025, at Muscoot Farm in Katonah, NY. The event features a 5-mile race for adults and two kids' races: one for ages 7-12 and another for children aged 6 and under. Participants can enjoy the scenic beauty of the farm while promoting awa..

The Bimblers Bluff 50K is an off-road foot race held in southern Connecticut, starting at Guilford Lakes School. The course features rolling forest roads and rocky single tracks, providing a challenging experience for runners. Unlike many similar events, participants do not complete the same loop mu..

The Grills Trail Run is a running event taking place at Grills Preserve in Westerly, Rhode Island, as part of the WTAC Fall Race Series. Participants can choose between a 10-mile and a 10K course, both of which feature scenic trails, bridges, and riverfront views within the Grills Wildlife Sanctuary..

The Fall Back Into The Trails Series is an annual running event hosted by C.T.W Endurance, taking place at the Red Wing Recreation Area in Lagrangeville, NY. Scheduled for November 1-2, 2025, the series features three race options: a challenging 100k, a 50k, and a 10k, each with varying elevation ga..

The "8 Hours at the Farm" event, organized by Steep Endurance, takes place at Gurski Farm/Williams Park in Brookfield, CT. This trail running challenge features a scenic 4-mile loop with a mix of single track and rolling farm trails, fostering a vibrant community atmosphere among participants. Runne..

The Pocantico Hills Marathon, taking place in Rockefeller State Park, offers both a marathon and a half marathon on scenic, rolling courses with views of the Hudson River and Palisades. Participants will enjoy a picturesque route featuring fields, stone walls, lakes, and forests. The event supports..

The Raven Rocks 10k is an annual trail race held at the Ward Pound Ridge Reservation in Cross River, NY. Set against a scenic backdrop, the race features a challenging course that includes rocky climbs, ridgeline trails, and hilly meadows. The event not only promotes fitness and outdoor activity but..

NYC Trail Mix is an exciting ultra trail running event taking place in Staten Island, New York, on November 15, 2025. This event features three race distances: a 50-mile, a 50K, and a half marathon, all set against the backdrop of over 35 miles of scenic trails. Participants will explore unique loca..

The Li'l Rhody Runaround Trail Run is a popular running event taking place at Burlingame State Park in Charlestown, Rhode Island. Scheduled for November 16, 2025, the event features two race options: an 8-mile course and a 4-mile course, both set against the scenic backdrop of Watchaug Pond. This ra..