Trail Running calendar near Winchendon 2025-2026

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 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 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 taking place in Sunapee, New Hampshire, on June 1, 2025. This race will serve as the 2025 USATF National Classic Mountain Championship and the sole selection race for the US Classic Up/Down Mountain Running Team, which will compete in Spai..

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 Norbrook Farm Brewery Trail Festival is a day-long outdoor event featuring various trail running and mountain biking races at Norbrook Farm Brewery in Colebrook, Connecticut. Participants can choose from events such as a 4-hour run, 10K, 5K, and a run/bike duathlon, along with challenging mounta..

The Nipmuck South Trail Race is a scenic 15.7-mile out-and-back race held at Mansfield Hollow State Park in Connecticut. Participants will enjoy a beautiful course that follows the Fenton River, featuring varied terrain, small bridge crossings, and a climb to a 50-foot cliff. The event includes thre..

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 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..

The Summer Solstice Trail Run is an early morning summer event held in Gay City State Park, featuring three race distances: 3 miles, 5 miles, and 8 miles. The race is part of the Blue-Blazed Trail Running Series and the USATF-CT Mountain, Ultra, and Trail Series, offering a competitive team element..

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 Flat Rock Trail Race is a new trail running event held in Dunstable, Massachusetts, benefiting the Humane Society for Greater Nashua's building expansion. Participants can run a 5-mile loop with nearly 600 feet of elevation gain, starting at the Arched Bridge and passing through scenic areas suc..

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 and sig..

The Cirque Series - Killington is an exciting running event set to take place in Killington, Vermont, featuring a challenging 7.2-mile course with an elevation gain of 3,133 feet. Participants can choose from three divisions: Sport (beginner/intermediate), Expert, and Pro, catering to various skill..

The Springfield Stars & Stripes 7.4K is a festive running and walking event held on Independence Day in Springfield, Vermont. Participants can choose between a 7.4K run or a 4K walk along the scenic Black River, starting and finishing at the Toonerville Trail trailhead. This inaugural event benefits..

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..

The 7-11 Slurpee Day Ultra 60k is a unique running event taking place in Vernon, CT, on July 11, 2025. Participants will cover a distance of 37.5 miles, primarily on roads, while making stops at various 7-11 locations along the route. This self-supported run encourages camaraderie and fun, with a so..

The Notchview Ultra is a multi-day ultramarathon event held from July 11-14, 2025, in Windsor, MA, at the scenic Notchview. Participants can choose from various race durations, including 6, 12, 24, 48, 72 hours, or a 100.7-mile race, starting at different times throughout the weekend. The course fea..

The Spaulding Woods 50K is a challenging trail race held in Northfield, New Hampshire, featuring a 5.6-mile technical loop with rocks, roots, and footbridges. Runners complete six laps over approximately 34 miles within a 10-hour time limit, with 4,400 feet of elevation gain. The course is primarily..

The Vermont 100 Endurance Race is a prestigious ultramarathon held annually in July, attracting endurance athletes from around the globe. This challenging event features a 100-mile race and a 100-kilometer option, with participants navigating a course that includes 17,000 feet of elevation gain thro..