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Obstacle Race Calendar near Middleburg 2025-2026

Explore the top obstacle runs near Middleburg for 2025-2026! We've gathered 106 exciting races in the area. Check out our detailed list below to find your next local race.

May 2026
May
16
Saturday

Two Twisted Posts Winery 10k

5 km 10 km
May
23
Saturday

National Wine Day 10k

5 km
May
30
Saturday

The More Miles Last One Standing Challenge

Backyard Ultra 4 mi
June 2026
Jun
28
Sunday

Heatwave Hustle 10k

5 km 10 km
August 2026
Aug
29
Saturday

The Inferno 10k

Trail Run 5 km 10 km
October 2026
Oct
25
Sunday

Halloween Horror 10k

Trail Run 5 km 10 km
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