Trail Running calendar near Red Hook 2025-2026

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 Book It for Books 10K and 5K is a charity running event held at Lake Accotink in Springfield, VA. Participants can choose to run or walk, with the event supporting literacy programs and providing books to children in need. The race features a trail course around the lake, with the 5K on the sout..

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..

The Saratoga Stryders Fall Back 5 Mile Trail Race is an exciting running event set in the scenic Saratoga Spa State Park. Participants can enjoy a challenging course that features a mix of hills, ridges, and single-track trails, showcasing the park's natural beauty. The race encourages runners to em..

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..

The Tarrywile Half Marathon, held at Tarrywile Park in Danbury, Connecticut, is a challenging trail race known for its significant elevation gain of nearly 3,000 feet and technical Northeast single-track terrain. The course offers stunning views of Danbury and the park's tranquil lakes. Runners can..

The Fall Fling 400 is an annual trail running event hosted by the CT Trailmixers at YMCA Camp Sloper in Southington, Connecticut. It features two main races: a 400-minute timed event where participants run as many loops as possible on a roughly two-mile trail course with varied terrain, including wo..

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 not only..

The Tower Tag Challenge is a trail running event held at Sleeping Giant State Park in Hamden, Connecticut, known for its scenic views and historic Observation Tower. Participants run repeated loops on the Tower Trail, a mostly smooth carriage road that ascends over 600 feet in 1.5 miles to the tower..

The Frosty Forest 5K is a trail running event held in Roosevelt Forest, Stratford, Connecticut. This 5K race offers participants a chance to escape the road and enjoy a scenic course through nature. Runners, joggers, hikers, and walkers are welcome, with a requirement of some trail experience.Partic..

The Sleeping Giant Trail Runs, held at Sleeping Giant State Park in Hamden, Connecticut, is a challenging trail running event known as one of the toughest in the Northeast. The race offers two distances: a 25K loop with over 3,000 feet of vertical gain and a 50K option for those who want to complete..

The Jack Bristol Lake Waramaug Ultra Races, taking place on April 27, 2025, is a celebrated ultra-running event in Connecticut, marking its 51st anniversary. This historic race features three distances: 100K, 50 miles, and 50K, all set around the scenic Lake Waramaug. Participants can expect well-st..