Trail Running calendar near Valley Cottage 2024-2025

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 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 with minimal outside interactio..

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 26.2 miles, 50K, 50 miles, 100K, and 100 miles, allowing athletes to challenge the..

The Paine to Pain Trail Half Marathon is a unique running event set in the scenic woods and trails of five parks in Westchester County, New York. This race features a single-loop course that allows participants to experience diverse terrain, primarily consisting of dirt paths, while enjoying the nat..

Big Bear Squatchtoberfest is a trail running event hosted by Sassquad Trail Running in collaboration with the New York-New Jersey Trail Conference. Set in Harriman State Park, Tuxedo, NY, this event features a challenging half marathon and a 10K race, showcasing the park's rugged terrain and stunnin..

The Long Run - Fall Back is a unique running event taking place at Jacobsburg State Park, featuring a 5-mile loop on a mix of single track and gravel trails. Participants can choose to compete in a 5-mile race, a 3-hour, or a 6-hour event, with the course run in reverse for this rendition. The event..

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

Rob's Trail Run Edition is a running event taking place at Stillwell Woods Preserve in Woodbury, NY. Scheduled for November 30, 2025, the event features two main races: a 5K Adult Trail Run for participants aged 19 and older, and a 5K High School or Youth Trail Run for those aged 18 and under. This ..

The Tower Tag Challenge is a trail running event held at Sleeping Giant State Park in Connecticut, featuring a scenic course that ascends over 600 feet to the Observation Tower. Participants can choose between 4-hour and 8-hour options, completing loops on the Tower Trail, which includes a mix of cr..