Trail Running calendar near Milton 2025-2026

The Hamsterwheel is an exciting ultrarunning event taking place in New Boston, NH, featuring races of 6, 12, 24, and 30 hours. Celebrating its 11th year, participants will run a scenic 4-mile loop along the New Boston Rail Trail, with opportunities for both individual and team entries. Runners can e..

The TARC Stone Cat Trail Festival, hosted by the Trail Animals Running Club, takes place at Willowdale State Forest in Ipswich, Massachusetts, offering a variety of race distances including 10K, half marathon, marathon, 50-mile, and 100K, along with a free youth fun run. Established in 2001, this ev..

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, participants can choose between two distances: an 8-mile and a 4-mile trail run. This event is part of the WTAC Fall Race Series, offerin..

The Baystate Dirty Dog Trail Run-Ruck-Walk 5k is a unique event taking place 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 TARC Winter Classic, organized by the Trail Animals Running Club, takes place at the scenic Middlesex Fells Reservation in Stoneham, Massachusetts. This popular trail running event offers participants the choice of 8-mile, 32-mile, and 40-mile distances, showcasing a challenging course filled wi..