Trail Running calendar near Brookline 2025-2026

The Flints Pond Trail Run is a new event aimed at raising funds for the Birches School while offering a scenic and challenging course on the Lincoln Land Trust Trails at Flint's Pond. The run takes place in a beautiful natural setting, providing participants with an enjoyable outdoor experience. Ame..

The Womp Romp Women’s Group Run is a welcoming running event held at Wompatuck State Park in Hingham, Massachusetts. Participants can choose to run distances ranging from 5 to 10 miles or more, accommodating various paces and preferences. The park offers a scenic and historic setting, featuring exte..

The Manchester 2 Monadnock Ultramarathon is a challenging 55-mile point-to-point race held in southern New Hampshire, starting in Manchester and finishing at Mount Monadnock State Park. The course features a mix of terrain: 60% roads, 20% dirt roads, and 20% trails, including a final ascent via the..

The Taunton Trail Half Marathon, held at Taunton Rugby Football Club in Somerset, offers an ultra-flat and fast course ideal for both beginners and experienced trail runners. The route features beautiful natural scenery along Taunton's waterways, providing an exhilarating running experience. Partici..

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 held in Sunapee, New Hampshire, serving as the 2025 USATF National Classic Mountain Championship and the selection race for the US Classic Up/Down Mountain Running Team. The race covers approximately 9.3 to 9.4 miles with about 3,250 to 3,..

The Drummer Hill Trail Races, held in Keene, New Hampshire, offer runners a choice of distances including 12.5K, 25K, 37.5K, and 50K, based on completing multiple laps of a 12.5K loop. The course features varied terrain, from technical single track to old jeep roads, with significant elevation chang..

The Nipmuck South Trail Race is a 15.7-mile out-and-back trail run held at Mansfield Hollow State Park in Mansfield, Connecticut. The scenic course follows the Fenton River and features varied terrain including small bridge crossings, a climb to a 50-foot cliff, fields, and woods. Runners encounter..

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

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..

Last Human Standing in West Greenwich, Rhode Island, is a unique endurance running event held on private property near the Big River Management Area. Participants race on a looped course, each lap requiring completion within 60 minutes to continue. The race begins at 10 AM, with subsequent laps star..

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 Springfield Stars & Stripes 7.4K is a festive Independence Day event held in Springfield, Vermont, starting and finishing at the Toonerville Trail trailhead. Participants can choose between a mostly flat 7.4K run or a 4K walk along the scenic Black River. The event supports the Springfield High..

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, self-supported ultramarathon held in Vernon, Connecticut, covering approximately 37.5 miles along mostly road routes. Participants run between seven 7-11 convenience stores across towns including Vernon, Manchester, East Hartford, West Hartford, Newington,..

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..