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Trail Running calendar near Winchendon 2026-2027

We have found 142 Trailruns within 80 miles of Winchendon. See below where and when you can find the races.

Mount Hood Nutcracker Challenge

Melrose - 52 mi from Winchendon

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.

February 2027

Tarctic Frozen Yeti

Westwood - 53 mi from Winchendon

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.

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