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Trail Running Calendar near Oconomowoc 2025-2026

Explore the top trail runs near Oconomowoc for 2025-2026! We've gathered 47 exciting races in the area. Check out our detailed list below to find your next local race.

February 2026
Feb - Mar
28-1
Sa - Su

ARKTOS

Backyard Ultra 6 hr 12 hr 20 hr
March 2026
Mar
14
Saturday

Shake Your Shamrocks

2 mi 5 km 10 km
April 2026
Apr
4
Saturday

DockHounds Dash

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

Prickly Pine Jackpot 24 Hour

Backyard Ultra 6 hr 12 hr 24 hr
May
17
Sunday

Wisconsin Pickle Run

2 mi 5 km
May
23
Saturday

Cedarburg Half Marathon

3 mi 13 mi
June 2026
Jun
13-14
Sa - Su

Kettle Moraine

Trail Run 50 km 38 mi 100 km 100 mi
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