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Trail Running Calendar near Sleepy Hollow 2026-2027

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Explore the top trail runs near Sleepy Hollow for 2026-2027! We've gathered 42 exciting races in the area. Check out our detailed list below to find your next local race.

June 2027
Jun
5
Sa

Squatchy Hooky: Lake to Summit

Road Race Trail Run 5 km 10 km
Jun
6
Su

Fire Tower Trail Races

Trail Run 10 km 13 mi
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