Trail Running calendar near Westwood 2026-2027

Enjoy a 4 mile run through Mine Falls Park followed by a festive post race party and raffle at Martha's Exchange. Support the Nashua Children's Home in this community event hosted by the Gate City Striders.

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.

Celebrate 20 years of festive racing with a unique 3.5 mile cross country run or 2 mile walk through the hilly landscapes of Melrose. Enjoy a pasta lunch and compete for coveted nutcracker awards at this local December tradition.

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.