Trail Running calendar near Brewster 2025-2026

TARCkey Trot 6 Hour at Wright Locke Farm in Winchester, MA is a six-hour trail race on a 5K loop. Laps feature rocky, rolling terrain that rewards focus, with runners choosing how many to complete within the time limit. The course is clearly marked with flagging and signs; a GPX file is available, a..

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

Turkeywacker 5K is a Thanksgiving morning trail run held in Wrentham, Massachusetts, at the William Rice Recreation Complex (54 Emerald Street). Now in its ninth year, the scenic 5K course winds through the complex’s trail system, welcoming runners and walkers of all ages. After the race, participan..

The TARC Winter Classic is a trail-running event staged at Middlesex Fells Reservation in Stoneham, Massachusetts. Runners choose among 8, 32, or 40 miles on the Skyline Trail, a challenging route of roots, rocks, and elevation with classic New England forest scenery and occasional views of the Bost..

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

TARCtic Frozen Yeti takes place at Hale Reservation in Westwood, MA, with a 15-mile loop and a 30-hour ultra option. The course is a tri-loop layout centered on a heated lodge at Powissett Lodge, with three roughly five-mile leaves marked by color-coded loops; runners can complete a single 15-mile l..

Join Trail Animals Running Club for the TARC Spring Classic at Jericho Town Forest in Weston, Massachusetts. The event offers 10K, Half Marathon, Marathon, and 50K distances, with a flat, smooth course crafted around a single 10K loop repeated for longer distances. Start/Finish at 292 Concord Road.C..

The Wildcat 5K Trail Run-Walk-Wag is an annual event held in Boxford, Massachusetts, starting and finishing at the Danvers YMCA Camp overlooking scenic Stiles Pond. The race features separate courses for runners and walkers, including those with dogs ("waggers"), winding through the Wildcat State Fo..