Trail Running calendar near Milton 2025-2026

The Tarckey Trot 6 Hour - Winchester, MA will take place in Winchester on Saturday 15 November 2025.

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 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 TARC Winter Classic, organized by the Trail Animals Running Club, is a trail running event held at the Middlesex Fells Reservation in Stoneham, Massachusetts. Participants can choose from 8-mile, 32-mile, and 40-mile distance options, navigating a challenging course featuring roots, rocks, and e..

The TARCtic Frozen Yeti is an exciting trail running event organized by the Trail Animals Running Club, taking place at Hale Reservation in Westwood, Massachusetts. Scheduled for February 7-8, 2026, participants can choose between a 30-hour race or a 15-mile distance. The course features three loops..