Trail Running calendar near Chesterfield 2025-2026

The Spring Fling 600 is an annual trail running event hosted by the CT Trailmixers at YMCA Camp Sloper in Southington, Connecticut. The event features two main races: the 600-minute race where participants run as many loops as possible on a roughly three-mile trail course within 10 hours, and a 6-mi..

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, with the course featuring rocky ledges..

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 Free Spirit 50k is a scenic ultramarathon held in Leyden, Massachusetts, featuring a challenging dirt road course with 4,200 feet of elevation change. Runners experience beautiful New England landscapes, including forests, fields, and a historic 1870s covered bridge. The event starts and finishe..

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 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 Flints Pond Trail Run is a new event aimed at raising funds for the Birches School while offering a scenic and challenging course on the Lincoln Land Trust Trails at Flint's Pond. The run takes place in a beautiful natural setting, providing participants with an enjoyable outdoor experience. Ame..

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 challenging 13.1-mile course features a mix of paved and dirt roads with significant elevation changes, including a stee..

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 Fitzwilliam to Troy Depot Day Cheshire Rail Trail Fun Run is a 5-mile running event taking place along the scenic Cheshire Rail Trail, starting from the original Fitzwilliam Railroad Depot to the newly restored Troy Depot. This event celebrates the historical significance of the rail trail, whic..

The Sunapee Scramble is a challenging mountain running event held in Sunapee, New Hampshire, serving as the 2025 USATF National Classic Mountain Championship and the sole selection race for the 2025 US Classic Up/Down Mountain Running Team. The race covers approximately 9.3 to 9.4 miles with about 3..

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 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 is a challenging trail running event held in Keene, New Hampshire, featuring multiple race distances including 50K, 37.5K, 25K, and 12.5K. Runners can choose the number of laps they wish to complete, with options for a single loop or multiple laps for longer distances. T..

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..