Trail Running calendar near Winsted 2025-2026

The Dandelion Dash and Mushroom Mile is a fun running event taking place in Hadley, MA, featuring a 5K trail run or walk and a 1-mile race suitable for participants of all ages. Scheduled for May 4, 2025, the event aims to support The Hartsbrook School's unique programming, which includes land stewa..

The Breakneck Point Trail Runs, organized by Red Newt Racing, is a challenging trail running event set to take place on May 4, 2025, in Beacon, NY. Participants can choose between a half marathon (13.1 miles) and a full marathon (26.4 miles), both featuring significant elevation gains and technical..

The Blue 2 Blue Challenge is a demanding 50K trail race set in New Haven, Connecticut, known for its challenging terrain and technical trails. Participants will navigate some of the toughest trails in the state, including the Regicides and Quinnipiac Trails, with a total elevation gain of approximat..

The Ansonia Trails 5K is a running event taking place in Ansonia, CT, designed for participants of the 169 Society. This second annual race features a unique course consisting of two laps around a 1.55-mile loop, making it slightly over or under a traditional 5K distance. Limited to 50 runners, the..

The TARC Wapack and Back is a challenging trail running event organized by the Trail Animals Running Club, taking place along the scenic Wapack Trail in Ashburnham, Massachusetts. Participants can choose from three distances: 21.5 miles, 43 miles, and 50 miles. The course features rugged terrain wit..

The Macho Trail Run is an exciting running event taking place in Stillwell Woods Preserve, Woodbury, NY. Scheduled for May 17, 2025, the event features two main races: a 5-mile Adult Trail Run and a 5-mile High School or Youth Trail Run. Participants will experience a unique trail running challenge..

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 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 designed for 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 pa..

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. The event emphasizes community and environmental stewards..

The Ocean State Ultra is an exciting running event taking place on May 24, 2025, at Big River State Management Area in West Greenwich, Rhode Island. Participants can choose from three race categories: 100 miles, 12 hours, and 6 hours. The course features a mix of desert, pavement, and trails, with a..

The Mine Hill Half Marathon, hosted by Steep Endurance, is touted as one of the toughest road half marathons in Connecticut. Set against the picturesque backdrop of the Mine Hill Distillery in Roxbury, participants will enjoy stunning views of farms and fields while navigating a challenging course...

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 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 Sri Chinmoy 24-Hour, 12-Hour, and Midnight Marathon is a running event taking place at Rockland Lake State Park, NY. This scenic race features a flat, 2.95-mile paved loop, ideal for both first-time ultra runners and those aiming for personal records. The event emphasizes high standards of runne..

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 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, and a run/bike duathlon. The festival also offers delicious food from lo..

The Nipmuck South Trail Race is a scenic 15.7-mile out-and-back race held in Mansfield, Connecticut, primarily along the beautiful Fenton River. Participants will encounter diverse terrain, including small bridge crossings and a climb to a 50-foot cliff. The event features three water stops and supp..

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 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, long c..