Trail Running calendar near Great Barrington 2025-2026

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 Plattekill Mountain Race, held in Roxbury, NY, is a challenging trail running event featuring a 6.5-mile course with 3,500 feet of elevation gain. Set on the ski slopes and trails of Plattekill Mountain, the race offers a rigorous mountain challenge ideal for athletes seeking to test their limit..

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 the Van Vleck Farm & Nature Sanctuary in Woodbury, Connecticut. Covering 3.1 miles, the course winds through scenic natural trails, offering a picturesque outdoor experience suitable for all ages and fitness levels. The event is..

The Death by Staircase Trail Running Festival, held in Moreau, NY, is a unique trail running event centered around a challenging 3.8-mile loop featuring the notorious "staircase of death." This rugged course climbs over 800 feet in less than a mile before descending sharply and finishing with a fast..

The Drummer Hill Trail Races, held in Keene, New Hampshire, offer runners a choice of distances including 12.5K, 25K, 37.5K, and 50K, based on completing multiple laps of a 12.5K loop. The course features varied terrain, from technical single track to old jeep roads, with significant elevation chang..

The Beer Mountain Challenge at Upward Brewing Company is an exciting trail running event set in the scenic Catskill Mountains. Participants can choose between two distances: a 2-mile loop with 515 feet of elevation gain or a 4-mile loop with 1,030 feet of elevation gain. The course features a mix of..

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 TSR Trail Half Marathon will take place in Adams on Sunday 15 June 2025. You can run between 10 and 21 kilometers.

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 held in the Catskill Mountains, starting in Windham, New York. The course follows the northern Black Dome Trail and the Long Path from Acra Point to downtown Phoenicia. Featuring approximately 15,000 feet of elevation gain, the route is rugged..

The Free to Run Trail Races, hosted by the Berkshire Ultra Running Community for Service (BURCS), take place in Pittsfield State Forest, Massachusetts. Scheduled for June 21, 2025, the event offers three distances: 15K, 25K, and 50K ultramarathon. The challenging course features a double-loop figure..

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 Centurion Ultra Trail Event, held in Roosevelt Forest, Stratford, Connecticut, is a challenging endurance race featuring a 2.5-mile loop with 193 feet of elevation gain per lap through classic New England terrain. Participants can choose between two race options: running as many miles as possibl..

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..

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..