Trail Running calendar near Charlestown 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 Watuppa Trail Races is an annual running event held in Fall River, Massachusetts, celebrating its 11th year in 2025. Participants can choose from three race distances: 10K, 30K, and 50K, catering to various skill levels and preferences. The event takes place in the scenic Watuppa Reservation, pr..

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 Dash For Dane & Family Day is an annual event held at Powisset Farm in Dover, MA, designed to honor the memory of Dane and support important causes. The event features a 5K Trail Run/Walk, a 1K Kids Fun Run/Walk, and various family-friendly activities such as magic shows, crafts, and live music...

The Run Ragged Last Person Standing is a challenging endurance event held in Berlin, Connecticut, hosted by the CT Trailmixers. Set on the rugged, hilly, and technical terrain of Ragged Mountain, runners tackle a roughly 3.11-mile loop every hour, starting at 8:00 AM. Participants must complete each..

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 4K Trail Run is a unique running event taking place in Boston, featuring individual and corporate team registrations. Scheduled for May 21 and 22, 2025, participants can join as individual runners or as part of a corporate team. The event aims to support Boston's youth through fundraising effort..

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 Womp Romp Women’s Group Run is a welcoming running event held at Wompatuck State Park in Hingham, Massachusetts. Participants can choose to run distances ranging from 5 to 10 miles or more, accommodating various paces and preferences. The park offers a scenic and historic setting, featuring exte..

The Taunton Trail Half Marathon, held at Taunton Rugby Football Club in Somerset, offers an ultra-flat and fast course ideal for both beginners and experienced trail runners. The route features beautiful natural scenery along Taunton's waterways, providing an exhilarating running experience. Partici..

The Powisset Farm Trail Run - Spring is a part of the Barn to Run Trail Race Series, taking place on Memorial Day, May 26, 2025, at Powisset Farm in Dover, MA. Participants can choose from four race distances: 8.3 miles, 5.6 miles, 3.1 miles, and 1.5 miles, all set against the scenic backdrop of Pow..

The Wine Run at Sakonnet Vineyard is a unique running event scheduled for June 7, 2025, in Little Compton, RI. Participants can enjoy a scenic trail run through the vineyard, culminating in a festive atmosphere with dinner, wine, and live music. The course spans approximately 3 miles and features va..

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 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 TARC Blue Hills Skyline Trail Run is a challenging 12K race set in the scenic Blue Hills Reservation in Milton, Massachusetts. Participants will tackle approximately 2,300 feet of elevation gain on a rugged course featuring rocky terrain, steep climbs, and technical descents, all while enjoying..

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 Last Human Standing event in West Greenwich, RI, is an endurance race held on private property near the Big River Management Area. Participants race on a loop, with each lap starting every hour and requiring completion within 60 minutes. Racers continue to run successive laps until only one rema..

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 Centurion Ultra Trail Event is an endurance race held in Roosevelt Forest, Stratford, Connecticut, featuring two main race options: a 33-hour challenge to run as many miles as possible or to complete 100 miles within 33 hours. The course is a 2.5-mile loop through classic New England terrain, in..