Trail Running calendar near Woodbury 2025-2026

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 Suffolk County Marathon is an annual running event held in Bay Shore, New York, featuring a variety of races including a full marathon, half marathon, 10K, and 5K. Scheduled for October 18-19, 2025, the marathon and half marathon take place on Sunday, while the 5K is held on Saturday. The races ..

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, New York, this event features a challenging half marathon and a 10K race, showcasing the park's rugged terrain and s..

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 participants aged 6 and older, alongside two kids' races: one for ages 7-12 and another for children aged 6 and under. The race aims to showcase the beauty of Mu..

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 with five loops, and a 10k. Participants c..

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

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

The Raven Rocks 10k is an annual trail race held at the Ward Pound Ridge Reservation in Cross River, NY. Scheduled for November 9, 2025, this challenging course features rocky climbs, ridgeline trails, and scenic views, making it a favorite among trail running enthusiasts. Participants can also enga..

The Brookhaven Trail Half Marathon is a premier running event organized by the Strong Island Running Club, taking place in Brookhaven State Park. This event features a challenging half marathon distance along with a 5-mile option, catering to runners of various skill levels. Participants can enjoy t..

The Tarrywile Half Marathon is renowned as one of the toughest trail half marathons, featuring nearly 3,000 feet of elevation gain and technical Northeast single track terrain. Set in Tarrywile Park, the course offers stunning views of Danbury and its serene lakes. Participants can choose from three..

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 and a 5K High School or Youth Trail Run, catering to participants of different age groups. This event aims to ..

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 is approximately 3.3..