Trail Running Calendar Massachusetts 2025-2026

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 TSR Trail Half Marathon will take place in Adams on Sunday 15 June 2025. You can run between 10 and 21 kilometers.

The Free to Run Trail Races, hosted by the Berkshire Ultra Running Community for Service (BURCS), take place in Pittsfield State Forest, Massachusetts. Scheduled for June 21, 2025, the event offers three distances: 15K, 25K, and 50K ultramarathon. The challenging course features a double-loop figure..

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 Flat Rock Trail Race, held in Dunstable, Massachusetts, features a challenging 5-mile loop with nearly 600 feet of elevation gain. The scenic course includes landmarks such as the Arched Bridge Conservation Area, an old railroad bed, a former granite quarry and farm, and climbs to the tops of Bl..

The Woodland Trail Series, hosted by Tri-Valley Front Runners, is a popular trail running event held at West Hill Dam in Uxbridge, Massachusetts. Celebrating its 27th year, the series features three races on well-marked courses through mostly wooded single and double track trails, with some gravel a..

The Notchview Ultra, held in Windsor, Massachusetts, is a multi-day ultrarunning event featuring various race durations including 100.7 miles, 72 hours, 48 hours, 24 hours, 12 hours, and 6 hours. The course is a scenic, well-maintained 1.9-mile perimeter loop trail around Notchview, with runners pas..

The Sweltering Summer Ultra is an annual running event held at Clapp Park in Pittsfield, Massachusetts. The 13th edition features an 8-hour race on a certified 0.355-mile dirt and cinder track, with runners switching directions halfway through. Participants can run or walk as many laps as they choos..

The Tarc Summer Classic will take place in Medfield on Saturday 16 August 2025. You can run between 10 and 40 miles.

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 Jug End Loop Ultra is a 6-hour ultra running event held at Jug End State Reservation in Egremont, Massachusetts. Participants run multiple laps of a challenging 4.2-mile course featuring woods, fields, and an apple orchard, with an elevation change of 830 feet per lap, split evenly between uphil..

The TARC Fall Classic will take place in Carlisle on Saturday 6 September 2025. You can run between 10 and 50 miles.

The Wicked Mudder will take place in Southwick on Sunday 7 September 2025. You can run between 5 and 5 kilometers.

The Wine Run at Westport Rivers Vineyard & Winery is a scenic running event scheduled for September 14, 2025, in Westport, MA. Participants can enjoy a beautiful trail run through the vineyard, covering approximately 3 miles amidst picturesque farms and vines. After the race, attendees can indulge i..

Run for Nature in Lowell, MA, is a community-focused running event held at Shedd Park, featuring a 10K trail run, a 5K run/walk, and a 1-mile Kids Fun Run/Walk. The course winds through scenic trails in Shedd Park and Rogers Fort Hill Park, including a stretch along the Concord River Greenway, with..

The Houghton's Pond Trail Races feature two distances: a 7-mile race and a 3.7-mile race, set in the scenic DCR Blue Hills Reservation in Milton, MA. Participants will navigate rolling dirt roads and forest paths, with elevation changes of approximately 700 feet for the 7-mile course and 300 feet fo..

The Groton Town Forest Trail Races will take place in Groton on Sunday 5 October 2025. You can run between 3 and 9 miles.

The Mt. Tom Trail Race is an exciting running event set against the stunning backdrop of Mt. Tom, featuring challenging terrain and breathtaking views, particularly during peak foliage.Participants can choose from a solo 25k, a 2-person 25k relay, or a solo 10k. The race supports the Kestrel Land Tr..

The Weir River Farm Trail Race, scheduled for October 19, 2025, in Hingham, MA, features three race distances: 10 miles, 6.0 miles, and 3.4 miles. This annual event showcases the scenic trails of Weir River Farm and the surrounding Whitney and Thayer Woods. Participants can enjoy post-race cider don..