Trail Running calendar near Milton 2025-2026

The TARCkey Trot is a unique 6-hour timed running event set on a scenic 5K loop at Wright Locke Farm in Winchester, MA. Participants can run as many loops as they wish within the time limit, navigating a course filled with natural terrain challenges. The event promotes community engagement, offering..

The Li'l Rhody Runaround Trail Run is a popular running event taking place at Burlingame State Park in Charlestown, Rhode Island. Scheduled for November 16, 2025, the event features two race options: an 8-mile course and a 4-mile course, both set against the scenic backdrop of Watchaug Pond. This ra..

The Baystate Dirty Dog Trail Run-Ruck-Walk 5k is a unique outdoor event held in Berkley, MA, designed to honor military personnel, first responders, and their K-9 companions. Participants can choose to run, ruck with weighted packs, or walk the rugged 5k trail, all while reflecting on the sacrifices..

The Novemberfest Race is an annual 4-mile running event held in Nashua, New Hampshire, featuring a scenic course through Mine Falls Park. This community-focused race supports the Nashua Children's Home, with all proceeds benefiting the organization. The event also includes a raffle held at Martha's..

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 along the Skyline Trail, known for its technical terrain featuring roots, rocks, and elevation changes typical of New Engla..

The TARCtic Frozen Yeti is a winter trail running event held at Hale Reservation in Westwood, Massachusetts. It offers two distance options: a 30-hour ultra and a 15-mile race. The course features three roughly 5-mile loops marked with colored ribbons and reflective tape, starting and finishing at P..

The Merrimack River Trail Race will take place in Andover on Saturday 11 April 2026. You can run between 10 and 10 miles.

The TARC Spring Classic is a trail running event held annually at Jericho Town Forest in Weston, Massachusetts. It offers multiple distance options including 10K, Half Marathon, Marathon, and 50K, catering to runners of all levels. The course features a relatively flat, smooth 10K loop with addition..

The TARC Wapack and Back is a challenging trail running event held annually in Ashburnham, Massachusetts, along the scenic Wapack Trail. Offering three distance options—21.5 miles, 43 miles, and 50 miles—the race features rugged terrain with rocky ledges, boulder fields, granite slabs, and technical..