Trail Running calendar near Poughkeepsie 2025-2026

The Spring Fling 600 is an annual trail running event hosted by the CT Trailmixers at YMCA Camp Sloper in Southington, Connecticut. The event features two main races: the 600-minute race where participants run as many loops as possible on a roughly three-mile trail course within 10 hours, and a 6-mi..

The Bruynswick Winery Run for UCSPCA is a 4.5-mile cross-country race organized by the Shawangunk Runners, taking place at the scenic Kiernan Farm/Bruynswick Winery in Gardiner, NY. This event aims to support the Ulster County SPCA, which is facing increasing demands due to the rising number of anim..

3 Days at the Fair is a multi-day ultrarunning event held at the Sussex County Fairgrounds in Augusta, New Jersey. The event features a certified 1-mile flat loop course composed of pavement and crushed gravel, suitable for various race distances including 6, 12, 24, 48, 72, and 144-hour timed races..

The SMR Mayapple Trail Runs, scheduled for May 17, 2025, in South Mountain Reservation, NJ, invites runners to participate in its 16th annual event. Organized by the South Mountain Conservancy, the race features various distances including 5 miles, 10 miles, 20 miles, 50K, and 50 miles, along with a..

The Tails & Trails State Forest Run, scheduled for May 17, 2025, in Pittsfield, MA, features three race distances: 50K, 25K, and a 5 Miler. This event supports local animal rescue nonprofits, including Red Robin Song Animal Sanctuary, No Paws Left Behind, and Berkshire Bird Paradise, Inc. Participan..

The Run Ragged Last Person Standing event, hosted by the CT Trailmixers, is an exciting endurance race set in the rugged terrain of Ragged Mountain, Berlin, CT. Participants will tackle a challenging 3.11-mile loop, with one hour to complete each lap. The race continues until only one runner remains..

The MCW NJ Appalachian Trail Runventure is a unique running event scheduled for May 17, 2025, in Scotch Plains, NJ. Participants can choose between a marathon or a 40-mile run, both designed to provide a fully supported experience along the New Jersey Appalachian Trail. This event is also a fundrais..

The Nassau Suffolk Trail Marathon & 15 Miler is a premier running event taking place in Farmingdale, NY, on May 18, 2025. This event features two main races: a full marathon and a 15-mile trail run, both set in the scenic Bethpage State Park. Participants will enjoy a well-marked course that include..

The 16th Annual Farmington River Run 5K Trail Race is scheduled for May 18, 2025, at Winding Trails in Farmington, Connecticut. This scenic race takes place on a designated 5K trail within a 300-acre area surrounding Walton Pond. Participants can compete for awards in various categories, including o..

C'mon Armageddon is a challenging trail running event held in West Milford, New Jersey, featuring courses of 50K, 10 miles, and 5 miles. The race takes participants through rugged, technical terrain, including boulder fields, river crossings, and mountain peaks with scenic views, such as the New Yor..

The Spring Run The Farm event, scheduled for May 18, 2025, in Katonah, NY, features a 5-mile trail race and two kids' races. The main event is open to participants aged 6 and older, while the kids' races cater to ages 7-12 and 6 and under. The race takes place at Muscoot Farm, showcasing the area's..

The NSRF Long Island Lemonade Trail 5K is a vibrant running event taking place at Blydenburgh County Park on May 24, 2025. This trail run offers participants a refreshing experience with a mix of pavement, dirt roads, and hard-packed trails. The event includes a free Kiddie Dash and features post-ra..

The Forest Park Runners Classic 4 Mile Road and Trail Race is set to take place on May 25, 2025, at Victory Field Track in Woodhaven, NY. This event features a scenic 4-mile out-and-back course through the beautiful trails and roads of Forest Park. Participants can expect custom technical T-shirts a..

The Mine Hill Half Marathon, held in Roxbury, Connecticut, is known as the toughest road half marathon in the state. Starting and finishing at the scenic Mine Hill Distillery, the challenging 13.1-mile course features a mix of paved and dirt roads with significant elevation changes, including a stee..

The Chesterfield Gorge Ultra & 25k is a unique running event held at the Chesterfield Gorge Reservation, featuring a 'choose your own adventure' format. Participants can select from various distances, including 100 miles, 100k, 50 miles, 50k, and 25k, with staggered starts to manage the flow of runn..

The Peach Hill "Run For the Hill of It" 5K is a cross-country running and walking event taking place at Peach Hill Park in Poughkeepsie, NY. Participants will traverse scenic trails, reaching the highest point in the town for stunning views. Open to all ages, the event encourages both runners and wa..

The Plattekill Mountain Race, scheduled for June 1, 2025, in Roxbury, NY, features a challenging mountain course and a shorter 5k option. The main race covers 6.5 miles with 3,500 feet of elevation gain, traversing ski slopes and trails, making it ideal for experienced runners seeking a tough mounta..

The IronHike Endurance Series - Spring 2025 takes place at Mohawk Mountain Ski Area in Cornwall, Connecticut. This multi-day event, held over four days in June, offers a unique blend of hiking, trail running, and camping challenges. Participants can compete solo, with a trail buddy, or as a trail fa..

The Flanders Field & Forest 5K is an annual trail run and walk held at Flanders’ Van Vleck Farm & Nature Sanctuary in Woodbury. Covering 3.1 miles of scenic trails, the event welcomes participants of all ages and fitness levels. It is officially timed and features divisions for different age groups,..

The Sri Chinmoy 24-Hour, 12-Hour, and Midnight Marathon is a scenic ultramarathon event held at Rockland Lake State Park near New York City. Participants can choose between a 24-hour race, a 12-hour race, or a midnight marathon, all taking place on a flat, fast 2.95-mile paved loop around the lake...