Trail Running calendar near Windsor 2025-2026

The Plattekill Mountain Race, scheduled for June 1, 2025, offers an exhilarating challenge for runners of all levels. Participants can choose between a 6.5-mile mountain race featuring 3,500 feet of elevation gain and a 5k option that includes a scenic ascent and thrilling downhill finish. The event..

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 Death by Staircase Trail Running Festival is a unique running event set to take place in Moreau, NY, featuring a challenging 3.8-mile loop that includes the notorious "staircase of death," which ascends over 800 feet in less than a mile. Participants can choose to run solo or join a relay team,..

The Drummer Hill Trail Races, set in Keene, NH, offers a unique trail running experience with multiple distance options: 50K, 37.5K, 25K, and 12.5K. Participants can choose how many 12.5K laps to complete, allowing for a customizable challenge. The course features a mix of technical single track and..

The Norbrook Farm Brewery Trail Festival is an exciting outdoor event featuring a variety of trails for both runners and mountain bikers. Participants can enjoy a full day of activities, including a 4-hour run, 10K and 5K runs, a run/bike duathlon, and various mountain bike races. The festival also..

The Nipmuck South Trail Race is a scenic 15.7-mile out-and-back race held at Mansfield Hollow State Park in Connecticut. Participants will enjoy a beautiful course that follows the Fenton River, featuring varied terrain, small bridge crossings, and a climb to a 50-foot cliff. The event includes thre..

The Edge Hill Trail Race, scheduled for 2025, is a collaborative event with the Franklin Land Trust, celebrating the scenic trails and dirt roads of Ashfield. This race emphasizes a relaxed atmosphere, encouraging participants to enjoy the natural beauty while challenging themselves physically and s..

Manitou’s Revenge is a challenging 53-mile ultramarathon set in the scenic Catskill Mountains, starting in Windham, NY. The course features approximately 15,000 feet of elevation gain, with rocky and steep terrain that requires runners to be self-sufficient, as aid stations are limited. Participants..

The Summer Solstice Trail Run is an exciting early morning event held in Gay City State Park, featuring 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 Mountain, Ultra, and Trail (MUT) series, offering teams a..

The Free to Run Trail Races, organized by the Berkshire Ultra Running Community for Service (BURCS), will take place on June 21, 2025, in Pittsfield State Forest, Massachusetts. This event features three race distances: 15K, 25K, and 50K, designed to challenge participants with scenic trails and sig..

The Brooksvale 12-Hour event is a unique running challenge taking place in Hamden, CT, where participants can test their endurance over a 12-hour period on a scenic 4.25-mile loop with a total elevation gain of 500 feet. Runners can aim for various distances, including 50 miles, marathons, or 50k, m..

The Springfield Stars & Stripes 7.4K is a festive running and walking event held on Independence Day in Springfield, Vermont. Participants can choose between a 7.4K run or a 4K walk along the scenic Black River, starting and finishing at the Toonerville Trail trailhead. This inaugural event benefits..

The F.I.T. Sun Mountain Challenge, taking place in Peru, Vermont, offers a thrilling experience for runners of all levels with events including a 5K, 10K, and a 25K ultra challenge. Set against the stunning backdrop of Bromley Mountain, participants can enjoy beautiful trails and breathtaking mounta..

The Red Wing Trail Challenge, organized by Conquer The World Endurance, is set for July 6, 2025, in Lagrangeville, NY. Participants can choose between a 60K race featuring approximately 6,600 feet of elevation gain and a 15K race with about 1,650 feet of gain. The event promises a scenic trail exper..

The Notchview Ultra is an exciting multi-day running event scheduled for July 11-14, 2025, in Windsor, MA. Participants can choose from various race formats, including 100.7 miles, 72 hours, 48 hours, 24 hours, 12 hours, and 6 hours, all set on a scenic 1.9-mile loop trail. The event features well-s..

The 7-11 Slurpee Day Ultra 60k is a unique running event taking place in Vernon, CT, on July 11, 2025. Participants will cover a distance of 37.5 miles, primarily on roads, while making stops at various 7-11 locations along the route. This self-supported run encourages camaraderie and fun, with a so..

The Rails-to-Trails 5K in East Hampton is a point-to-point race starting at the Connecticut Draft Horse Rescue. Participants will be transported to the starting line via shuttle buses from Center School. The course features a scenic route along the Air Line Trail, concluding at the Old Home Days gro..

The Soapstone Assault is a challenging approximately 5-mile trail race held at Soapstone Mountain, featuring a unique course that requires participants to climb the mountain six times. This event is designed for those seeking a rigorous hill workout, as runners navigate steep, rocky, and potentially..

The People's Forest 7-Mile Trail Run, now in its 26th year, is a prominent event in the USATF/CT Mountain Ultra Trail series. Scheduled for August 2, 2025, in Barkhamsted, CT, this trail run offers participants a scenic and challenging course through the beautiful People's Forest. The event is open..

The Landis Arboretum 5K Forest Run is an annual event held in Esperance, NY, showcasing a scenic cross-country course through the Arboretum's forests and meadows. Participants can enjoy stunning views of the Schoharie Valley while competing in this 19th edition of the race. The event features age gr..