4.8
(23)
331
riders
30
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.
Last updated: May 27, 2026
72
riders
48.5km
01:56
190m
190m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(2)
28
riders
34.8km
01:27
240m
240m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Sign up for free
7
riders
51.2km
02:07
250m
250m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
6
riders
50.6km
02:08
240m
240m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
1
riders
51.2km
03:22
210m
210m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Login or Signup
Popular around Oconomowoc
Although a big part of the Drumlin Gracier Trail is paved, in this part of the trail, the path is made up of compacted dirt, which shouldn't be much trouble, just use extra caution during/after rain.
1
0
Kettle Moraine State Forest isn’t the best for road cycling, but it's worth locking up your bike and exploring on foot. This vast area, covering over 22,000 acres, boasts glacial hills, kettle lakes, and prairies. It offers more than 100 miles of trails for hiking, mountain biking, horseback riding, and nature walks. Enjoy paddling, boating, swimming, fishing, and hunting, as well as winter activities.
0
0
The Paradise Valley Wildlife Area, spans 1,800 acres across four parcels to offer public hunting and support habitat for various wildlife. The area features primarily emergent wetlands, surrounded by oak openings, savanna, grasslands, and former prairie agricultural land, catering to both game species and conservation efforts.
0
0
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.
0
0
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.
0
0
The park is a tribute to veterans and a cherished community gathering area. This is a good spot to take a break and enjoy the serene surroundings in this urban park.
0
0
The Five Points Historic District in Waukesha, at the intersection of Broadway, Main St., and Grand Ave, showcases the history of some of the city's most iconic buildings. Post-1857, the area transitioned from small wooden structures to grand Waukesha Lannon limestone buildings, creating a cohesive streetscape. Italianate and Queen Anne styles, with their distinctive turrets, are prominent, especially on corner sites. South Street, with its mix of styles and uses, remained residential into the 1880s.
0
0
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.
0
0
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.


Browse the best Road cycling routes in other regions.