Trail Running calendar near Brookline 2025-2026

The Mt. Tom Trail Race is an exciting running event set against the stunning backdrop of Mt. Tom, featuring challenging terrain and breathtaking views, particularly during peak foliage.Participants can choose from a solo 25k, a 2-person 25k relay, or a solo 10k. The race supports the Kestrel Land Tr..

The Weir River Farm Trail Race, scheduled for October 19, 2025, in Hingham, MA, features three race distances: 10 miles, 6.0 miles, and 3.4 miles. This annual event showcases the scenic trails of Weir River Farm and the surrounding Whitney and Thayer Woods. Participants can enjoy post-race cider don..

Womp Romp is an exciting running event taking place in Wompatuck State Park, Hingham, MA, featuring a 50K and a 10-mile race. Celebrating its fifth year, the event has consistently sold out, with a cap of 350 participants. The course includes a mix of single track, wide trails, and pavement, caterin..

The Powisset Farm Trail Run - Fall is a part of the Barn to Run Trail Race Series, taking place at Powisset Farm in Dover, MA. This event features four race distances: 8.3 miles, 5.6 miles, 3.1 miles, and 1.5 miles, catering to both experienced and novice trail runners. Participants can enjoy post-r..

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 a turnaround point at Lang's Station. The event encourages both i..

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 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 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 Mount Ascutney Vertical Backyard is a unique "Last Person Standing" running event held in Brownsville, VT. Participants will ascend and descend 1,209 vertical feet each hour, with options for different lap lengths. The challenge continues until only one runner remains, with the goal of matching..

The Krampuslauf is an exciting running event held at the Dartmouth Skiway in Lyme, NH, featuring 5K, 10K, and a challenging 9-hour endurance race. Participants will navigate scenic mountain trails, starting at the ski lodge and tackling both Holt's and Winslow sides of the mountain. Runners can earn..

The TARC Winter Classic, organized by the Trail Animals Running Club, takes place at the Middlesex Fells Reservation in Stoneham, Massachusetts. This trail running event offers participants the choice of 8-mile, 32-mile, and 40-mile distances, featuring a challenging course with roots, rocks, and el..

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..