Trail Running calendar near Hauppauge 2025-2026

The Storybook Half Marathon is a friendly trail running event held in Roosevelt Forest, Stratford, Connecticut. The course consists of 1.64-mile loops repeated eight times, totaling the half marathon distance of 13.1 miles. Runners, joggers, hikers, and walkers are all welcome, with a four-hour time..

The Wild Goose Trail Festival is a multi-day trail running event held at Wawayanda State Park in Hewitt, New Jersey. Taking place September 20-21, 2025, it offers a variety of race distances including a 1-mile kids run, 10K, half marathon, 50K, 50-mile, 100K, 100-mile, and a 36-hour endurance challe..

The Gardiner Dump Run is an exciting running event scheduled for September 21, 2025, in Gardiner, NY. Participants can choose between a 5k trail run or a 10k option, which consists of two laps of the 5k course. The race takes place on scenic single-track trails through wooded hillsides near the Wall..

The Cockaponsett Trails to a Cure is a running event taking place in Chester, Connecticut, featuring two trail races: a 4-mile and a 9-mile course through the scenic Cockaponsett State Forest. The course includes challenging terrain with roots, rocks, and hills, and is designed to accommodate runner..

The Angevine Farm Trail Festival, held annually in Warren, Connecticut, offers a scenic and challenging trail running experience in the Northwest corner of the state. The event features multiple distances including a half marathon, a new 8-hour race on a 1.25-mile farm loop, and 5K races including a..

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 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, held at Mohawk Mountain Ski Area in Cornwall, Connecticut, offers challenging trail running events including a marathon, half marathon, 10K, and 5K. The course features steep ascents and descents on ski mountain trails and rolling paths through Mohawk State Forest, providin..

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 in Katonah, NY, is a scenic 5-mile trail race held at Muscoot Farm, 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 highlights the natural beauty of..

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 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, Connecticut. The race features a rolling country course with an approximately 4-mile loop combining single track and farm trails, offering a scenic and community-focused atmosphere. Participants can choose..

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 Run is an annual trail race held at Ward Pound Ridge Reservation in Cross River, NY. Known for its challenging course, the race features rocky climbs, ridgeline trails, hilly meadows, ravines, and scenic views including the site of the former fire tower. The event fosters a vibra..