Trail Running calendar near Woodbury 2025-2026

The Spring Fling 600 is an annual trail running event organized by the CT Trailmixers, taking place at YMCA Camp Sloper in Southington, CT. This year marks the eighth edition, featuring two race options: a 600-minute challenge where participants can run as many loops as they wish on a roughly three-..

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..

The "Run Like A Mother" 5K Trail Run, organized by the Franklin Elementary School PTO, is a family-friendly event taking place at Giddings Park in North Franklin, CT. This Mother's Day-themed race celebrates the incredible role of mothers and is open to participants of all ages, including a special..

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 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 Soapstone Mountain Trail Races, taking place on May 18, 2025, in Stafford Springs, CT, features two scenic races: a 25K and a 6K "Sampler." Both courses wind through the picturesque Soapstone Mountain area and Shenipsit Forest State Park, offering a mix of challenging terrain and beautiful lands..

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 renowned as one of the most challenging road races in the state. Starting and finishing at the Mine Hill Distillery, the course offers stunning country views of farms, fields, and vistas. The race features a demanding route with significa..

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 IronHike Endurance Series - Spring 2025 takes place at Mohawk Mountain in Cornwall, CT, from June 5 to June 8, 2025. This unique event combines hiking and trail running, offering participants various challenges, including individual and team formats. Events range from 12 to 84 hours, with distan..

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...

The Ansonia Six Hour Trail Run is an exciting endurance event taking place at the Ansonia Nature Center in Ansonia, Connecticut. Participants will tackle approximately 1.9-mile loops on moderately technical singletrack trails, featuring about 170 feet of elevation gain per loop. Scheduled for the se..

The Norbrook Farm Brewery Trail Festival is a day-long outdoor event featuring various trail running and mountain biking races at Norbrook Farm Brewery in Colebrook, Connecticut. Participants can choose from events such as a 4-hour run, 10K, 5K, and a run/bike duathlon, along with challenging mounta..