Trail Running calendar near Wading River 2025-2026

The Nipmuck Trail Marathon, organized by the Shenipsit Striders, is a challenging 26.4-mile trail race held in Ashford, Connecticut. The course follows a rugged segment of the Nipmuck Trail, featuring rocks, roots, mud, and wood bridges, offering a demanding experience for trail runners. Participant..

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 a multi-distance ultramarathon event held in Rocky Point, NY, on October 10, 2025. Participants can choose from various races, including 150-mile, 100-mile, 100K, 50-mile, 50K, and 10-mile distances, with some races starting as early as Friday evening and others on Saturday an..

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 Mohawk Mountain Ski Area in Cornwall, CT. This challenging trail event features multiple race options, including a 5K, 10K, Half Marathon, and Marathon, with courses that incorporate the ski mountain's steep ascents and descents,..

The Paine to Pain Trail Half-Marathon is an annual trail running event held in Westchester County, New York, typically in October. It features a challenging course that winds through the woods and trails of five different parks, with most of the race on dirt, rocks, and roots, offering a scenic and..

Big Bear Squatchtoberfest is a trail running event held in Harriman State Park near Tuxedo, New York, on October 19, 2025. It offers a challenging half marathon and 10K course through rugged, technical trails featuring steep climbs, rocky terrain, and scenic views, especially during peak fall foliag..

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 a trail running event held in Lagrangeville, NY, at the Red Wing Recreation Area. Taking place over the weekend of November 1-2, 2025, it features multiple race distances, including a 50K, 10K, and a 100K ultramarathon. The event offers challenging courses wit..

8 Hours at the Farm is a trail running event held at Gurski Farm/Williams Park in Brookfield, CT. Participants can choose from an 8-hour, 4-hour, or 4-mile race, featuring a scenic, rolling course with single track and farm trails. The event fosters a community atmosphere, with runners seeing each o..

The Pocantico Hills Marathon, held in Sleepy Hollow, NY, takes place in Rockefeller State Park and features a scenic, rolling, and hilly course with views of the Hudson River and Palisades. Participants can choose between the full marathon and half marathon, both of which pass through picturesque la..

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..

The Tarrywile Half Marathon is a challenging trail race set in Tarrywile Park, Danbury, CT, featuring nearly 3,000 feet of elevation and technical Northeast single-track terrain. Participants can choose from a 10K, Half Marathon, or Marathon, with the course offering scenic views of Danbury and tran..

The Fall Fling 400 is an annual trail running event organized by the CT Trailmixers, featuring a unique 400-minute race where participants can complete as many loops as they wish on a two-mile course. Additionally, a 4-mile option is available, consisting of two laps of the same course. The event pr..

The Squatchy Leftovers Trail Race, taking place on November 29, 2025, at South Mountain Reservation in West Orange, NJ, offers a variety of distances including 5K, 10K, 25K, and 50K. This family-friendly event supports the non-profit organization Bigger Than The Trail, which provides cost-free thera..