Trail Running calendar near Guilford 2025-2026

The Run Ragged Last Person Standing is a challenging endurance event held in Berlin, Connecticut, hosted by the CT Trailmixers. Set on the rugged, hilly, and technical terrain of Ragged Mountain, runners tackle a roughly 3.11-mile loop every hour, starting at 8:00 AM. Participants must complete each..

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..

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, held in Stafford Springs, Connecticut, offer two scenic trail running events: a challenging 25K (approximately 15.5 miles) and the Jerry Stage 6K "Sampler." Both courses wind through the beautiful Soapstone Mountain area within Shenipsit Forest State Park, featuri..

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 race offers runners stunning country views of farms, fields, and vistas. The challenging course features a demanding fir..

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 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...

The Wine Run at Sakonnet Vineyard is a unique running event scheduled for June 7, 2025, in Little Compton, RI. Participants can enjoy a scenic trail run through the vineyard, culminating in a festive atmosphere with dinner, wine, and live music. The course spans approximately 3 miles and features va..

The Ansonia Six Hour Trail Run is a challenging endurance event held at the Ansonia Nature Center in Ansonia, Connecticut. Participants run counter-clockwise loops of approximately 1.9 miles on moderately technical singletrack trails featuring about 170 feet of elevation gain per loop. The course of..

The Norbrook Farm Brewery Trail Festival, held at Norbrook Farm Brewery in Colebrook, Connecticut, is a vibrant all-day event featuring trail running and mountain biking. Participants can choose from a 4-hour run, 10K, 5K, run/bike duathlon, and various mountain bike races on challenging 5-mile loop..

The Nipmuck South Trail Race is a 15.7-mile out-and-back trail run held at Mansfield Hollow State Park in Mansfield, Connecticut. The scenic course follows the Fenton River and features varied terrain including small bridge crossings, a climb to a 50-foot cliff, fields, and woods. Runners encounter..

The Summer Solstice Trail Run is an early morning trail running event held at Gay City State Park in Hebron, Connecticut. Scheduled for June 21, 2025, it offers three race distances: 3 miles, 5 miles, and 8 miles. The 8-mile race is part of the 2025 Blue-Blazed Trail Running Series and the USATF-CT..

The Last Human Standing event in West Greenwich, RI, is an endurance race held on private property near the Big River Management Area. Participants race on a loop, with each lap starting every hour and requiring completion within 60 minutes. Racers continue to run successive laps until only one rema..

The Brooksvale 12-Hour is an endurance running event held in Hamden, Connecticut, featuring a challenging 4.25-mile loop with 500 feet of elevation gain. Participants can choose to run distances ranging from a marathon (six loops) to a 50k (eight loops) or aim for 50 miles within the 12-hour time li..