Trail Running calendar near Brookline 2025-2026

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 is a multi-day ultrarunning event held in Windsor, Massachusetts, featuring a variety of 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 aid sta..

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 Ragged 75 Stage Race and 50K is a challenging trail running event held in Danbury, New Hampshire, centered around the scenic SRKG Greenway near Lake Sunapee. The 75-mile stage race spans three days, featuring steep climbs and technical single-track trails with about 15,500 feet of elevation gain..

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..

Lover's Lane in Chester, Vermont, is a unique 6- or 12-hour running event featuring a 1.8-mile loop course with 280 feet of elevation gain and loss per lap. The trail combines single and double-track paths along with jeep trails, offering a moderately challenging terrain. The race starts and finishe..

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

The Webb Forest Wander is a family-friendly 5K race held in the scenic Webb Forest trail system in Wilmot, New Hampshire. Organized by the Wilmot Learning Place, a nonprofit preschool, the event offers a well-marked course through a beautiful nature preserve maintained by the New London Conservation..

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 Triple Dam 10K is a scenic running and walking event held at the Power Dam Recreation Area in Perkinsville, Vermont. The course is a beautiful loop featuring gently rolling terrain on a mix of grassy trails, dirt roads, and single track, primarily on the west side of the Black River and North Sp..

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 Cross-Connecticut Run for Mental Health Awareness is a unique 56-mile group running event held annually in Connecticut, traversing the state north to south along the scenic and flat Farmington Canal Heritage Trail. Starting in West Suffield and ending at New Haven Harbor, the course passes throu..

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

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 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..