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Trail Running Calendar near Waukesha 2026-2027

Monthly updates for Waukesha

Get new running races (and updates) in your inbox every month.

Explore the top trail runs near Waukesha for 2026-2027! We've gathered 14 exciting races in the area. Check out our detailed list below to find your next local race.

May 2026
May
9
Sa

Ice Age Trail 50

Trail Run 13 mi 50 km 50 mi
May
16
Sa

Conservation Chase

Trail Run 3 mi 6 mi 13 mi
June 2026
Jun
13-14
Sa - Su

Kettle Moraine

Trail Run 50 km 38 mi 100 km 100 mi
Jun
20
Sa

Whitewater Trail Challenge

Trail Run 10 km Half Marathon 50 km
July 2026
Jul
11
Sa

Feel the Burn

Trail Run
August 2026
Aug
1
Sa

Casual Hikers 10K

Trail Run 10 km
September 2026
Sep
25
Fr

Echo 136

Trail Run 136 mi
October 2026
Oct
3
Sa

Lapham Peak Colorama Run/walk

Trail Run 5 km 10 km
Oct
4
Su

The Milwaukee Beer Run 5k

Trail Run 5 km
Oct
10
Sa

Zachariah's Acres Fall Run

Trail Run 3 mi 13 mi
Oct
11
Su

Race for Open Space - West Bend

Trail Run 5 km 10 km
Oct
31
Sa

Among the Trees

Trail Run 50 km 100 km
November 2026
Nov
7
Sa

Warrior 8K Through the Park

Trail Run 5 km 8 km
Nov
14
Sa

Bucks & Does 13.1

Trail Run 3 mi 6 mi 13 mi
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