Trail Running calendar near Westwood 2026-2027

TARC Winter Classic offers 8 32 and 40 mile trail races on the rugged Middlesex Fells Skyline Trail with roots, rocky climbs and occasional Boston skyline views. Affordable entry and proceeds support land conservation.

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.

A 123 mile point to point ultramarathon across Connecticut featuring about 57 miles of trail, a 36 hour cutoff, solo and relay options, and belt buckles for 200K finishers.