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Trail Running Calendar near Winchester 2026-2027

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Explore the top trail runs near Winchester for 2026-2027! We've gathered 21 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

June 2027
Jun
5
Sa

The More Miles Last One Standing Challenge

Backyard Ultra 4 mi
Backyard-style ultra in Knoxville MD with repeating 4.167 mile laps every hour until one remains, plus a concurrent 1 mile Mortals edition.
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