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Road cycling routes
United States
Wisconsin
Waukesha County

Oconomowoc

The best road cycling routes around Oconomowoc

4.8

(22)

292

riders

28

rides

Want to go road cycling around Oconomowoc? We’ve reviewed all of the road rides around Oconomowoc to identify the best. Explore them all here, and find your perfect road cycling route around Oconomowoc.

Last updated: November 24, 2025

70

riders

1. Dousman to Waukesha via Glacial Drumlin State Trail — Waukesha County

48.5km

01:56

190m

190m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate
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