Trail Running calendar near Holyoke 2025-2026

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 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 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, offering a mix of challenging terrain and beautiful lands..

Ocean State Ultra is an exciting running event taking place at Big River State Management Area in West Greenwich, Rhode Island. Scheduled for May 24, 2025, the event features three race categories: a challenging 100-mile race, a 12-hour endurance challenge, and a 6-hour race. Participants can expect..

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

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 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 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 Drummer Hill Trail Races, set in Keene, NH, offers a unique trail running experience with multiple distance options: 50K, 37.5K, 25K, and 12.5K. Participants can choose how many 12.5K laps to complete, allowing for a customizable challenge. The course features a mix of technical single track and..

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, a run/bike duathlon, and various mountain bike races. The festival also..

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 will take place in Canton on Saturday 21 June 2025. You can run between 12 and 12 kilometers.

The Edge Hill Trail Race will take place in Ashfield on Saturday 21 June 2025. You can run between 8 and 50 kilometers.

The Summer Solstice Trail Run is an exciting early morning event held in Gay City State Park, featuring 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 Mountain, Ultra, and Trail (MUT) series, offering teams a..

The Last Human Standing - West Greenwich, RI will take place in West Greenwich on Saturday 21 June 2025.

The Flat Rock Trail Race is a new trail running event taking place in Dunstable, Massachusetts, with proceeds benefiting the Humane Society for Greater Nashua's building expansion. Participants will navigate a scenic 5-mile loop featuring nearly 600 feet of elevation gain, including diverse terrains..

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..