Trail Running calendar near Brookline 2026-2027

Discover the beauty of Emmons Preserve at a community event featuring trail races and family activities. Enjoy music and local treats while supporting holistic education through a variety of distances for runners and walkers.

Experience an obstacle course race inside the historic Fenway Park stadium. This event features a 5K course with 20 obstacles and dedicated races for children through the iconic home of the Boston Red Sox.

Experience a classic New England trail event at Willowdale State Forest featuring multiple distances from 10K to 100K. Run through rolling terrain on a course celebrated for its community spirit and long history.

A backyard ultra at Kenty's Farm on a 4.1666 mile loop where runners repeat hourly laps until one remains. Timed options of 6, 12 and 24 hours and single-lap entries are also available.

TARCkey Trot is a 6 hour trail challenge at Wright Locke Farm of repeated 5K loops with rocky rollers. Run as many loops as you wish and bring your own hydration for this cupless event.

A Last Person Standing mountain event in Brownsville, VT where runners repeat hourly climbs totaling large elevation gains. Options include a higher turnaround of about 1,209 feet or repeated t bar repeats; aid and indoor facilities are pro..

Enjoy a festive four mile trail race through the wide paths of Mine Falls Park. All proceeds from the run and raffle support residential and educational programs at the Nashua Childrens Home.

TARC Winter Classic in Stoneham offers 8, 32 and 40 mile trail races on the white blazed Skyline Trail with rugged roots, rocks, frequent climbs and Boston skyline views. Expect technical trails, minimal markings and a festive finish.

Race Mozey brings the Central European Krampus Run tradition to New England. Choose from a 5K, 10K, or a 9-hour challenge to complete laps at the Dartmouth Skiway. Finishers get medals, and the event supports Vermont Adaptive Ski and Sports..

Celebrate the twentieth anniversary of this unique cross country race held at the Mount Hood Golf Club. Choose between a competitive three and a half mile run or a festive two mile walk through hilly terrain.

Experience a winter trail challenge at Hale Education featuring 15 mile and 30 hour options. Navigate three unique loops through the Massachusetts woods while testing your endurance and self reliance in cold weather conditions.