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United States
Wisconsin
Waukesha County

Oconomowoc

The best road cycling routes around Oconomowoc

4.8

(26)

418

riders

33

rides

Road cycling around Oconomowoc, Wisconsin, is characterized by its glacial topography, featuring rolling hills and numerous lakes. The region is nestled within the "Heart of Lake Country," offering diverse and scenic routes that pass by bodies of water like Lac La Belle and Fowler Lake. Cyclists can expect varied terrain shaped by ancient glaciers, including woodlands and open countryside.

Best road cycling routes around Oconomowoc

  • The most popular road cycling route is Glacial Drumlin State Trail, a 30.1 miles…

Last updated: October 10, 2026

4.7

(3)

32

riders

#1.

Glacial Drumlin and Lake Country Trail Loop

34.8km

01:27

240m

240m

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

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Easy

6

riders

50.6km

02:08

240m

240m

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

Moderate
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19

riders

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

Easy

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

Easy

8

riders

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

Easy
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Popular around Oconomowoc

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Cycling around Oconomowoc

Tips from the Community

maniboyflex
June 24, 2025, Historic Long Barn on Lake Country Trail

Connecting Oconomowoc to Nemahbin Lakes, the Lake Country Trail offers open views and lakeside scenery. It’s a fun, low-traffic stretch with a mix of urban and countryside, passing by big barns along the way.

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As you ride the Glacial Drumlin State Trail past the UWM Waukesha Field Station, you’ll pass prairies, wetlands, and even an old kiln. It’s a fun spot to slow down, spot some wildlife, or take a quick detour on the Field Station trails before jumping back on the main route.

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The Meadowbrook Trail, along the Route of the Badger, is 2.4 miles and winds through a blend of neighborhoods and business districts. This paved route offers a mostly open path with sparse shade, bordered by a broad grassy median away from the road. Cyclists should pack extra water for the ride to stay hydrated.

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The Cushing Park Road Recreational Trail, part of the Route of the Badger, stretches for 3 miles. Though short, it serves as a crucial link in the regional trail system, connecting the Lake Country Recreation Trail to the north and the Glacial Drumlin State Trail to the south. Cyclists can also access the Ice Age Trail from this pathway.

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The Glacial Drumlin State Trail stretches 53 miles from Cottage Grove to Waukesha, offering a scenic journey through southeastern Wisconsin's glacial history. Formed during the last Ice Age, this area features wetlands, ponds, rivers, and numerous drumlins—low, cigar-shaped hills. The trail intersects with the 1,200-mile Ice Age Trail for approximately 2 miles near Wales, providing a unique blend of cycling and hiking opportunities through this geologically rich landscape.

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Nagawicka Lake spans 981 acres and reaches depths of up to 90 feet, making it ideal for boating, swimming, and fishing. The lake is home to diverse fish species, including Panfish, Largemouth Bass, Smallmouth Bass, Northern Pike, and Walleye, offering a great fishing experience. This picturesque lake provides plenty of recreational opportunities for visitors.

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The Lake Country Trail, spanning 15.2 miles, takes cyclists from Waukesha to Oconomowoc through Wisconsin's picturesque Lake Country. This route, largely following an old Milwaukee-Watertown Interurban Railway path, features farmland and rolling hills, with occasional glimpses of Pewaukee and Upper Nemahbin Lakes. In Delafield, the trail intersects with the Cushing Park Road Recreational Trail, which leads to the Glacial Drumlin State Trail. Nearby, Naga-Waukee Park offers recreational activities such as swimming, boating, and fishing in Nagawicka and Pewaukee lakes, making it a perfect stop along the trail.

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Amy
September 28, 2022, Pewaukee Lake

This is the largest lake in Waukesha County. You can paddleboard, kayak, fish, sail, canoe and waterski here. There's heaps of amenities around the lake like cafes too.

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Frequently Asked Questions

How many road cycling routes are available around Oconomowoc?

There are over 30 road cycling routes around Oconomowoc, offering a variety of experiences. These routes cater to different skill levels, with 21 easy routes and 13 moderate routes available for exploration.

What kind of terrain can I expect on road cycling routes in Oconomowoc?

The terrain around Oconomowoc is characterized by its unique glacial topography, featuring rolling hills and numerous lakes. You'll encounter varied landscapes, from open countryside and farmlands to scenic lakeside views and woodlands, shaped by ancient glaciers.

Are there any easy or family-friendly road cycling routes in the area?

Yes, Oconomowoc offers several easy and family-friendly options. For instance, the Glacial Drumlin State Trail is an easy route following an old railway line, perfect for a relaxed ride. The Glacial Drumlin and Lake Country Trail Loop also combines easy segments for varied scenery.

What are some scenic highlights or natural features I can see while cycling?

Oconomowoc's routes are rich in natural beauty. You'll find picturesque lakeside views, especially along routes near Lac La Belle, Fowler Lake, and Pewaukee Lake. The area also features diverse habitats like woodlands, wetlands, and prairies in places such as the Oconomowoc River Conservancy Park and Nature Hill Nature Center. The glacial landscapes themselves are a prominent feature, particularly along the Glacial Drumlin State Trail.

Do I need a permit or pass to cycle on trails like the Lake Country Trail or Glacial Drumlin State Trail?

Yes, some state trails in Wisconsin, including portions of the Lake Country Trail and Glacial Drumlin State Trail, may require a Wisconsin State Trail Pass for cyclists aged 16 and older. It's advisable to check the specific requirements before you ride.

What is the best time of year for road cycling in Oconomowoc?

The spring, summer, and fall seasons generally offer the best conditions for road cycling in Oconomowoc. Spring brings fresh greenery, summer provides warm weather for lakeside rides, and fall showcases beautiful foliage. Always check local weather conditions before heading out.

Are there any specific landmarks or attractions along the cycling routes?

Beyond the natural beauty, you can encounter several points of interest. The Lake Country Trail itself is a significant feature, and you might catch glimpses of lakes like Nagawicka Lake and Pewaukee Lake. Nearby, Lapham Peak Observation Tower offers expansive views, and downtown Oconomowoc provides a charming area to explore.

Where can I find parking for the cycling trails in Oconomowoc?

Roosevelt Park in Oconomowoc serves as an excellent trailhead with amenities and parking, especially for accessing the Lake Country Trail. Other access points for trails like the Glacial Drumlin State Trail may also have designated parking areas; it's recommended to check specific trailheads.

Can I bring my dog on the road cycling trails?

Policies regarding dogs on multi-use trails can vary. While some trails may allow leashed dogs, others might have restrictions. For specific trails like the Lake Country Trail, it's best to verify the current dog policy with the local trail authority to ensure a pleasant and compliant ride.

What do other road cyclists enjoy most about cycling in Oconomowoc?

The road cycling routes in Oconomowoc are highly rated by the komoot community, with an average score of 4.8 stars from over 20 reviews. Cyclists often praise the varied scenery, the well-maintained trails, and the blend of lakeside views with rolling glacial landscapes that make for an engaging ride.

Are there places to stop for refreshments or find bike rentals in Oconomowoc?

Yes, downtown Oconomowoc offers various places to take a break and grab refreshments. The city actively promotes cycling, and you can find local spots for bike rentals if you don't bring your own. For more information on local amenities, you can visit the Visit Oconomowoc website.

How can I access Oconomowoc's cycling routes using public transport?

While Oconomowoc is primarily accessed by car, some public transportation options exist. Waukesha County Transit provides services that may offer access to areas near cycling routes. It's advisable to check their schedules and routes for specific connections to trailheads.

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Browse the best Road cycling routes in other regions.

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