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Obstacle Race Calendar near Shepherdstown 2025-2026

Explore the top obstacle runs near Shepherdstown for 2025-2026! We've gathered 24 exciting races in the area. Check out our detailed list below to find your next local race.

August 2025
Aug
9
Saturday

Third Winchester Battlefield Half

Trail Run 5 km 10 km 13 mi
Aug
16
Saturday

Gary Brown Memorial C&O Canal Run

5 mi
Aug
16
Saturday

Miner's Lady 8-Hour

Trail Run 10 km
Aug
23
Saturday

I Believe In Me 5K

5 km
Aug
24
Sunday

Sweet Run 10k

5 km 10 km
Aug
30
Saturday

Kalero 5k

5 km
September 2025
Sep
6
Saturday

The Inferno 10k

Trail Run 10 km
Sep
6
Saturday

Lock 2 Lock Marathon

10 km 13 mi 26 mi
Sep
20
Saturday

Run On The Rocks

10 mi 13 mi 20 mi
Sep
27
Saturday

Runnin' with the Dogs 5K

5 km
October 2025
Oct
4
Saturday

Freedom's Run

5 km 10 km 13 mi 26 mi
Oct
11
Saturday

Run the Vineyards Williams Gap

5 km
Oct
26
Sunday

Ghostly Grapes 10k at Two Twisted Posts

5 km 10 km
November 2025
Nov
30
Sunday

Henway Hard Cider Turkey Trot 10k

5 km 10 km
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