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Trail Running Calendar near Woodbury 2026-2027

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

September 2027
Sep
19
Su

Gardiner Dump Run

Trail Run 5 km 10 km
Trail races at Gardiner’s Riverbend Trails with 5K and 10K options, sneaker recycling with coupons, pre registration T shirts, and breakfast sandwiches.
October 2027
Oct
16
Sa

Big Bear SquaTCh South

Trail Run 10 km 13 mi
Trail half marathon and 10K at Harriman State Park in Tuxedo NY, co-hosted by Sassquad and the New York-New Jersey Trail Conference; proceeds support trail maintenance.
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