Shepherdstown close

Obstacle Race Calendar near Shepherdstown 2025-2026

Explore the top obstacle runs near Shepherdstown for 2025-2026! We've gathered 37 exciting races in the area. Check out our detailed list below to find your next local race.

October 2025
Oct
26
Sunday

Ghostly Grapes 10k at Two Twisted Posts

5 km 10 km
November 2025
Nov
2
Sunday

Friends 10K

5 km 10 km
Nov
15
Saturday

Berryville Turkey Trot 5K

5 km
Nov
27
Thursday

Landsdowne Turkey Trot

5 km
Nov
27
Thursday

Sheppard Pratt Frederick Turkey Trot

5 km
Nov
30
Sunday

Henway Hard Cider Turkey Trot 10k

5 km 10 km
December 2025
Dec
6
Saturday

Candy Cane Dash 5K - Frederick

5 km
Dec
7
Sunday

South Berkeley Christmas 5K

5 km
Dec
27
Saturday

Summit Point Half

5 km 10 km 13 mi
April 2026
Apr
18
Saturday

SMHS Makin' Hay 10K

5 km 10 km
May 2026
May
2-3
Sa - Su

Frederick Running Festival

5 km 13 mi
May
9
Saturday

Deer Dash 5K

5 km
May
9
Saturday

The Bettie Jane Cancer Foundation 5K Run/Walk

5 km
May
9
Saturday

Tiki Trot 5K

5 km
May
23
Saturday

Amani Brewing 5K

5 km
May
25
Monday

Panda 5K

5 km
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