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Trail Running Calendar near Waukesha 2025-2026

Explore the top trail runs near Waukesha for 2025-2026! We've gathered 64 exciting races in the area. Check out our detailed list below to find your next local race.

March 2025
Mar
15
Saturday

Shake Your Shamrocks

3 km 5 km 10 km
Mar
15
Saturday

Lucky Leprechaun 7K

7 km
Mar
15
Saturday

Grafton Lucky 5K

5 km
Mar
15
Saturday

Watertown Jig Jog 5K

5 km
Mar
16
Sunday

Luck of the Irish

5 km 10 km
Mar
22
Saturday

Time to Paddy Half Marathon - Milwaukee

5 km 10 km 13 mi
Mar
23
Sunday

First Call Half Marathon

5 km 10 km 13 mi
Mar
23
Sunday

Lucky Dog 5K

5 km
April 2025
Apr
5
Saturday

DoNot Stop Half Marathon - Milwaukee

5 km 10 km 13 mi
Apr
5
Saturday

South Shore Half Marathon - Milwaukee

13 mi
Apr
6
Sunday

Run the Trailbreaker

Trail Run 5 km 10 km 13 mi 26 mi
Apr
6
Sunday

Sweet Home Milwaukee 5K

5 km
Apr
12-13
Sa - Su

Milwaukee Marathon

5 km 13 mi 26 mi
Apr
12
Saturday

Run From The Tax Man

5 km 10 km 13 mi
Apr
13
Sunday

DockHounds Dash

2 mi 5 km
Apr
19
Saturday

Brew City Marathon

5 km 10 km 13 mi 26 mi
Apr
26
Saturday

The Non Cancelled Marathon

5 km 10 km 13 mi 26 mi
Apr
26
Saturday

Cream City 5K

3 km 5 km
May 2025
May
3-4
Sa - Su

Prickly Pine Jackpot 24 Hour

Backyard Ultra 6 hr 12 hr 24 hr
May
3
Saturday

Cinco K Mayo

5 km
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