Trail Running calendar near Winchester 2025-2026

The Spaulding Woods 50K is a challenging trail race held in Northfield, New Hampshire, featuring a technical 5.6-mile loop with rocks, roots, and footbridges. Runners complete six laps totaling approximately 34 miles with 4,400 feet of elevation gain, primarily on singletrack trails. The event suppo..

The 12 Hours of Lawrence Woods is a half-day ultrarunning event held in Medford, Massachusetts, within the scenic Lawrence Woods section of the Middlesex Fells Reservation. Participants run a roughly 5-mile loop course that stays within the woods without crossing over itself, sharing only one inters..

Ocean State Ultra is an endurance running event held at Big River State Management Area in West Greenwich, Rhode Island. The race offers three categories: a 100-mile ultra, a 12-hour, and a 6-hour race, all conducted on a 10-mile loop course featuring 1.5 miles of desert, 1 mile of pavement, and 7.5..

The Soapstone Assault is a challenging approximately 5-mile trail race held at Soapstone Mountain, featuring a unique course that requires participants to climb the mountain six times. This event is designed for those seeking a rigorous hill workout, as runners navigate steep, rocky, and potentially..

The Kingman Farm Trail Race is a welcoming and challenging running event designed for participants of all skill levels. Spanning approximately 3.6 miles, the course features Nordic-style paths and switchback singletrack, making it an exciting experience for runners. This event is organized by acidot..

The Anchor Down Ultra is a seaside ultra-marathon event held at Colt State Park in Bristol, Rhode Island. It features multiple race options including 6-hour, 12-hour, and 24-hour ultra-marathons, catering to endurance runners of various levels. Known as "The Smallest State's Longest Races," it has b..

The GTA Challenge will take place in Greenfield on Saturday 16 August 2025.

The Tarc Summer Classic is a trail running event held at Noon Hill Reservation in Medfield, Massachusetts, featuring multiple race distances including 10 miles, 50K, and 40 miles. The course is a scenic, mostly forested loop with undulating terrain, roots, rocks, and a notable viewpoint at Noon Hill..

Greenbelt's Vineyard Hill Trail Run is an annual trail running event held in South Hamilton, Massachusetts, located on the scenic town line of Hamilton and Topsfield. The race offers 5K and 10K distances that challenge runners with a course featuring Vineyard Hill, sections of Bradley Palmer State P..

The TARC Fall Classic is a popular trail running event held at Great Brook Farm State Park in Carlisle, Massachusetts, offering a range of distances including 10K, half marathon, 20 mile, 50K, and 50 mile races, plus a Yeti Mischief Mile and a free youth fun run. The courses wind through scenic New..

The Veterans Count Nashua 5k Fun Run & Walk will take place in Nashua on Sunday 14 September 2025. You can run between 5 and 5 kilometers.

The Wine Run at Westport Rivers Vineyard & Winery is a scenic trail running event held in Westport, Massachusetts. The approximately 3-mile course winds through beautiful farms and finishes among the vineyard’s grapevines. After the run, participants enjoy a festive atmosphere with dinner, wine, and..

The Gunstock 5K and Canicross 5K take place at Gunstock Mountain Resort in Gilford, NH, as part of the 3rd annual Food Truck Festival. The event features a 5K trail run and a Canicross 5K where participants run with their dogs on a loop course of gravel roads and cross-country ski trails with rollin..

The Pisgah Mountain Trail Races, held in Pisgah State Park, Chesterfield, New Hampshire, feature two challenging trail distances: a 50K and a 23K. Organized by the Red Clover Rovers, this event supports the New Hampshire Special Olympics, with all profits benefiting their mission. The races start fr..

The Mt. A Trail Challenge is an annual running event held at the summit of Mount Agamenticus in York, Maine. The 9th edition features two distances: a 5K and a 1 Mile course, suitable for running, hiking, rolling, or strolling.The race is timed manually by the local York High School Cross Country Te..

The Hooksett Kiwanis 5K Trail Race, held in Hooksett, New Hampshire, is a scenic trail run starting at Heads Pond trail and finishing at the Hooksett Public Library. The course features a hard-packed stone dust surface transitioning into a wooded conservation trail, offering a natural and enjoyable..

The ACT Trail Fest, held in Arundel, Maine, is an annual trail running event organized by the Arundel Conservation Trust. Participants can choose from a 5k, 10k, or half marathon course that winds through the scenic ACT Multi-Purpose Trail and Eastern Trails, featuring beautiful woodland and stream..

The Bear Brook Trail Races, held in Allenstown, New Hampshire, showcase the scenic beauty of Bear Brook State Park with its diverse trails, including single track paths, steep hills, and blueberry fields. The event offers three race distances: a 10K following "Mindy's Loop," a Half Marathon, and a M..

The Survival of the F.I.T.test - 30+ Hour Trail Ultra is a challenging endurance event held in Cumberland, Rhode Island. Participants can choose between two course options: a flat, fast 2.1-mile loop or a more rugged 4.2-mile trail loop used in previous years. The event offers multiple race formats..

Run for Nature in Lowell, MA, is a community-focused running event held at Shedd Park, featuring a 5K Run/Walk, a 10K Trail Run, and a Kids 1-Mile Fun Run/Walk. The course traverses scenic double- and single-track trails through Shedd Park and Rogers Fort Hill Park, including a stretch along the Con..