Trail Running calendar near Boston 2025-2026

The Run For Ryan Memorial Run is a family-friendly event held in Dayville, Connecticut, featuring a 5K run, a walk, and a kids fun run. The race honors Ryan French, a local high school athlete and scholar, with proceeds supporting the Ryan French Memorial Scholarship Fund for deserving Ag-Ed seniors..

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 starting on the same day. The course features 10-mile loops combining 1.5 miles of desert, 1..

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 Stonington Cross Country 5K is a free running event held at Stonington High School in Pawcatuck, Connecticut. The course begins with a loop on the school track, followed by a half-mile run on quiet, dead-end streets within the campus. Runners then transition to a mix of single- and double-track..

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..

The Shenipsit Striders 50th Fatass is a celebratory running event held at Crandall's Park Pavilion in Tolland, Connecticut. Marking the club's 50th anniversary, the event features an 8-hour window where participants run multiple 5K loops on a trail course starting and finishing at the pavilion. Runn..

The Midstate Massive Course Preview is a pre-race recon run held in Spencer, Massachusetts, offering runners a chance to explore a 13.1-mile section of the Midstate Trail used in both the 50-mile and 100-mile races. The run covers the trail segment between Aid Stations 6 and 8, providing participant..

The GTA Challenge is a 10K trail race held in Greenfield, New Hampshire, organized by the Greenfield Trail Association to support local trail maintenance. The course features a mix of class 6 roads, double track, and single track trails with natural obstacles like rocks and roots, offering a challen..

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 Run to Fall 5K is an annual cross-country race held at Coe-Brown Northwood Academy in Northwood, New Hampshire. Celebrating its 25th edition in 2025, the event features a 5K cross-country race, a 2.5-mile trail walk, and youth USATF 3K races for different age groups. A kids' fun run around the t..

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 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 take place in Bear Brook State Park, Allenstown, New Hampshire, offering a marathon, half marathon, and 10K race. The courses feature scenic single-track trails, steep climbs, and expansive blueberry fields, showcasing the park's natural beauty. The marathon consists of ru..