Trail Running calendar near Charlton 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.

Challenge yourself on the historic Tower Trail at Sleeping Giant State Park. Choose between 4 or 8 hours to complete as many 3.3 mile loops as possible on this scenic gravel path to the Observation Tower.

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.