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Trail Running Calendar near Oconomowoc 2026-2027

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Explore the top trail runs near Oconomowoc for 2026-2027! We've gathered 25 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

October 2027
Oct
9
Sa

Ultratrax Alpine Valley

Trail Run 7 mi 14 mi 21 mi 28 mi
Timed 10 hour trail event at Alpine Valley, Elkhorn WI with clearly marked single track loops of 7, 14, 21 and 28 miles and optional weighted divisions.
Oct
9-10
Sa - Su

Helios

Trail Run
Timed 6, 12 and 20 hour trail ultraruns in Eagle Wisconsin with solo and relay options across three loop distances and manual lap timing.
Oct
16
Sa

Golden Kettle Trail Series - Scuppernong

Trail Run 3 mi 5 mi 11 mi 19 mi
Trail races at Scuppernong Trailhead in Kettle Moraine State Forest with 3.1, 5.4 and 10.8 mile loops plus a 19.3 mile combined option.
Oct
30
Sa

That's an Awful Idea 5K - Let's Do It

Trail Run 3 mi
A fall event in Oconomowoc with multiple running and ruck options, featuring 3.1 mile courses, a 0.5 mile hill race, and a free kids climb.
Oct
30
Sa

Among the Trees

Trail Run 50 km 100 km
Trail ultramarathon on the Ice Age Trail offering 100k and 50k routes, wooden medal branding, aid stations, and fall foliage in the Southern Kettle Moraine Forest.
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