Trail Running calendar near Brewster 2025-2026

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..

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 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 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 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..

The Aggie Ram Trail Run 5k will take place in Walpole on Sunday 5 October 2025. You can run between 5 and 5 kilometers.

The Houghton's Pond Trail Races take place in the scenic DCR Blue Hills Reservation in Milton, Massachusetts, just south of Boston. This event offers two trail race distances: 7 miles and 3.7 miles, both starting and finishing near the Houghton's Pond Visitor Center. The courses feature rolling terr..

The Weir River Farm Trail Race, held annually in Hingham, Massachusetts, offers runners three trail distances: 10 miles, 6 miles, and 3.4 miles. The race courses wind through the scenic trails of Weir River Farm, Whitney, and Thayer Woods, with the 10-mile route including additional loops in Wompatu..

The Ravenswood Trail Race will take place in Gloucester on Sunday 19 October 2025. You can run between 4 and 4 miles.

Womp Romp is an annual trail running event held at Wompatuck State Park in Hingham, Massachusetts, scheduled for October 25, 2025. The race offers two distances: a 10-mile single loop and a 50K consisting of three loops plus an additional mile. The course features a mix of single track, wide trails,..

The Powisset Farm Trail Run - Fall is a popular trail running event held at Powisset Farm in Dover, Massachusetts. Scheduled for October 26, 2025, it offers four race distances: 8.3, 5.6, 3.1, and 1.5 miles, traversing scenic trails through Powisset Farm and the neighboring Noanet Woodlands. The rac..

The TARC Stone Cat Trail Festival will take place in Ipswich on Saturday 1 November 2025. You can run between 10 and 100 kilometers.

The Tarckey Trot 6 Hour - Winchester, MA will take place in Winchester on Saturday 15 November 2025. You can run between 6 and 6 hours.

The Baystate Dirty Dog Trail Run-Ruck-Walk 5k, held in Berkley, Massachusetts, is a rugged outdoor event honoring military personnel, first responders, and their K-9 companions. Participants can run, ruck with weighted packs, or walk a challenging 5k trail through scenic natural landscapes. The even..

The TARC Winter Classic is a trail running event held annually at Middlesex Fells Reservation in Stoneham, Massachusetts. It offers challenging distances of 8, 32, and 40 miles on the technical Skyline Trail, featuring roots, rocks, and elevation changes typical of New England terrain. Runners exper..

The Mount Hood Nutcracker Challenge is an annual cross-country running event held in Melrose, Massachusetts, at the Mount Hood Golf Club. This unique 3.5-mile race features a challenging, hilly course that changes every year, incorporating fairways, paved cart paths, road crossings, and occasional w..

The TARCtic Frozen Yeti is a winter trail running event hosted by the Trail Animals Running Club at Hale Reservation in Westwood, Massachusetts. It offers two distance options: a 15-mile race and a challenging 30-hour endurance race. The course features three roughly 5-mile loops marked with colored..

The TARC Spring Classic is a trail running event held annually at Jericho Town Forest in Weston, Massachusetts. Offering 10K, Half Marathon, Marathon, and 50K distances, the course features a relatively flat, smooth 10K loop with twisting trails suitable for all skill levels. Runners complete multip..