Winding Trails Trail Running Series

The Sleeping Giant Trail Runs, set in the iconic Sleeping Giant State Park in Hamden, Connecticut, promises to be one of the toughest trail races in the Northeast. Participants can choose between a challenging 25K or a grueling 50K course, featuring over 30 miles of diverse terrain, including smooth..

The Traprock 50 is a challenging trail running event held at Penwood State Park in Bloomfield, CT, featuring two race distances: a 50K and a 17K. The course consists of approximately 10.5-11 miles per loop, with the 50K requiring three loops and the 17K one loop. Runners will navigate a mix of techn..

The Blue 2 Blue Challenge is a demanding 50K trail race set in New Haven, Connecticut, known for its challenging terrain and technical trails. Scheduled for May 4, 2025, this event features a rigorous out-and-back course that includes significant elevation gain and rocky paths, making it suitable fo..

The Mine Hill Half Marathon, held at the scenic Mine Hill Distillery in Roxbury, Connecticut, is touted as one of the toughest road half marathons in the state. Participants can expect a challenging course that offers stunning views of farms, fields, and picturesque landscapes. The event features a ..

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 Norbrook Farm Brewery Trail Festival is an exciting outdoor event featuring a variety of trail races and mountain biking activities. Set in the picturesque Norbrook Farm Brewery, participants can enjoy a day filled with adventure, including a 4-hour run, 10K and 5K runs, and a run/bike duathlon...