Trail Running calendar near Wading River 2025-2026

The Wicked Mudder will take place in Southwick on Sunday 7 September 2025. You can run between 5 and 5 kilometers.

The Macedonia Trail Race, held in Macedonia Brook State Park near Kent, Connecticut, offers a unique trail running experience with lush singletrack trails, challenging climbs and descents, and stunning viewpoints including Cobble Mountain, where runners can see the Catskill Mountains on clear days...

The Pawling 24 Hour Trail Running Festival, held in Pawling, NY at Lakeside Park, offers runners a challenging and festive endurance experience. Participants can choose from 3, 6, 12 (including a night start), or 24-hour timed races on a 1.68-mile loop course featuring pavement, grass, and single-tr..

Run for the Hills is an annual 5K trail run and walk held at the Oswegatchie Hills Nature Preserve in Niantic, Connecticut. The event offers participants a scenic course around Clark Pond and along the preserve's perimeter, showcasing over 450 acres of coastal forest. Designed as a fundraiser, proce..

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 Wahaneeta Trail Run is a 5K trail race held in Westerly, Rhode Island, located on Moorhouse Road. Scheduled for September 13, 2025, it is the first event in the WTAC Fall Trail Race Series, which includes four races with a discount for registering in multiple events. This race embraces an "old s..

The Charlie Stavros Memorial Beach Run is a free, 3-mile race held at Westerly Town Beach in Westerly, Rhode Island. Organized by the Westerly Track Club and the Stavros family, this event takes place at low tide, featuring a scenic out-and-back course of 1.5 miles each way along the beach. The run..

The Angevine Farm Trail Festival is a scenic trail running event held in Warren, Connecticut, in the picturesque Northwest corner of the state. The festival features multiple race options including an 8-hour endurance run, a half marathon, and 5K races with a Canicross option for runners with dogs...

The Cockaponsett Trails to a Cure is a trail running event held in Chester, Connecticut, within the Cockaponsett State Forest. Participants can choose between a 4-mile or a 9-mile race, with the shorter distance comprising the first part of the longer course. The trail features natural terrain inclu..

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, held at Mohawk Mountain Ski Area in Cornwall, Connecticut, is a multi-day endurance event featuring rugged, scenic courses designed to challenge participants with significant elevation gains. Spanning from October 2 to 5, 2025, the series offers various timed events ra..

The Run for the Pumpkins Trail Run, held in Westerly, Rhode Island at Bradford Preserve, is part of the WTAC Fall Race Series. This event features 5K and 10K trail races, along with a free 1K children's run for ages 10 and under. The courses highlight preserved town land and the Woody Hill Managemen..

The Run the Vineyards - Pindar Fall 5K and 8K is a scenic autumn race held at Pindar Vineyards in Peconic, NY, featuring courses through 300 acres of vineyard property. Participants can choose between a 5K or 8K race on a mostly flat course consisting of hard-packed dirt trails and short-cut grass,..

The KMT Fall Foliage Frenzy is a timed trail running event held in Montebello, NY, featuring 3-hour and 6-hour race options. Participants run on a challenging 2.33-mile loop course in Kakiat Park, adjacent to Harriman State Park, with approximately 660 feet of vertical gain per lap. The course offer..

The NipMuck Trail Marathon, held in Ashford, Connecticut, is a challenging 26.4-mile trail race along the scenic Nipmuck Trail. The course features diverse terrain including rocks, roots, mud, and wood bridges, with a route that heads south to Route 44, returns to the start, then goes north to Bosto..

The Norfolk Land Trust Trail Race Series, including the Haystack Mountain Challenge, is held annually in Norfolk, Connecticut. The event features three trail races: a 5K, 10K, and a challenging half marathon. The 5K course runs through scenic Barbour Woods with a mix of single and double track trail..

The Tesla Hertz Run is an ultramarathon event held in Rocky Point, New York, featuring multiple race distances including 150 miles, 100 miles, 100K, 50 miles, 50K, and 10 miles, with both daytime and nighttime options. The course is a scenic 10.48-mile loop through the pine barrens of Long Island, o..

The Forbidden Forest 30 Hour Ultra Run is an epic endurance event held in Stratford, Connecticut, offering runners up to 30 hours to complete distances ranging from a marathon (26.2 miles) to 100 miles or more. The course features a challenging 2.23-mile loop with roots, rocky terrain, and a notable..

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 a distinctive trail race held in Westchester County, New York, starting at the historic Thomas Paine Cottage in New Rochelle and finishing at New Rochelle High School. This 13.1-mile single-loop course traverses the woods and trails of five different parks, o..