5.0
(10)
69
riders
15
rides
Touring cycling around Oconomowoc features a landscape characterized by numerous lakes and gently rolling terrain. The area offers a mix of paved bike trails and quiet roads, suitable for various cycling preferences. Elevation changes are generally modest, making the region accessible for recreational riders. The presence of several lakes, such as Nagawaukee Lake and Pewaukee Lake, provides scenic routes along their shores.
Last updated: July 2, 2026
5.0
(3)
13
riders
15.2km
00:54
50m
50m
The Bike loop from Good Shepherd Methodist Church offers a serene touring cycling experience, guiding you through picturesque rural landscapes. You'll pedal past open fields and farms, enjoying tranquil water views along the Little Bushkill Creek, all while being enveloped by extensive shade. Keep an eye out for local wildlife, as deer are often spotted along this peaceful route.
This easy 9.4-mile (15.2 km) loop involves a gentle 151 feet (46 metres) of elevation gain, typically taking about 54 minutes to complete. While the terrain is mostly level, much of the trail is crushed stone, so a mountain bike might offer a smoother ride than an electric road touring bike. Weekdays are ideal for a quieter experience, allowing you to fully appreciate the trail's calm atmosphere.
Originally a railroad line, this trail is now part of the Planefield Township Recreation Trail, known for its conversion into a recreational path. Its former life as a railway ensures a largely flat profile, making it accessible for many, while the abundant tree cover provides a welcome respite from the sun on warm days.
5.0
(3)
11
riders
12.7km
00:44
40m
40m
This easy 7.9-mile (12.7 km) touring bicycle loop, taking about 44 minutes with just 135 feet (41 metres) of elevation gain, offers a delightful spin through Oconomowoc's scenic surroundings. You'll pedal past tranquil lakes, including glimpses of Nagawaukee Lake, and through a pleasant mix of open countryside and suburban areas. The terrain is generally flat with only gentle ascents, making it a relaxing ride for almost anyone.
Planning your visit is straightforward, as Oconomowoc boasts a well-maintained network of cycling routes. While this specific loop's trailhead isn't explicitly named, many local access points, such as those near Roosevelt Park, provide convenient parking and amenities like restrooms. This route is ideal for a casual outing, perfect for families or those looking for a quick, low-effort ride on a pleasant day.
Oconomowoc is a hub for cycling, offering access to significant regional paths like the Lake Country Trail, which runs along a former railway line. This loop provides a taste of the area's diverse offerings, showcasing the charming downtown connections and the natural beauty of the glacial landscapes. It's a great way to explore the local area and its many cycling landmarks and viewpoints.

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5.0
(1)
12
riders
35.1km
02:01
120m
120m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
6
riders
25.3km
01:33
240m
240m
If you're seeking a diverse touring cycling experience in Waukesha County, the Pewaukee Lake loop from Nagawaukee Park & Ride delivers. This moderate 15.7-mile (25.3 km) route, with 784 feet (239 metres) of elevation gain, typically takes around 1 hour and 33 minutes to complete. You'll pedal through a mix of tranquil marshes, dense forest patches, and open fields, all while enjoying picturesque views of Pewaukee Lake and Nagawicka Lake, especially from the top of the route's notable climb.
Starting at the convenient Nagawaukee Park & Ride, which offers free parking and bike racks, you'll find this route well-supported. The Lake Country Trail, a key part of the loop, provides access to amenities like restrooms and water at various points. It's a great option for a morning or afternoon ride, particularly in spring when wildflowers add an extra splash of color to the scenery.
This loop largely follows the historic Milwaukee-Watertown Interurban Railway right-of-way, adding a touch of local history to your ride. The well-marked Lake Country Trail also shares nearly two miles with the Ice Age National Scenic Trail near Delafield, offering a unique connection to Wisconsin's natural heritage. It's a fantastic way to explore the Pewaukee Lake area, blending natural beauty with a touch of local history.
4
riders
45.3km
02:43
310m
310m
If you're seeking a diverse and engaging touring cycling experience in Waukesha County, the Nagawicka Lake loop from Okauchee Lake is a fantastic option. This moderate route, covering 28.1 miles (45.3 km) with 1018 feet (310 metres) of elevation gain, guides you through a tapestry of farmland, quiet forests, and wetlands. You'll enjoy continuous waterfront views of Nagawicka Lake and pass through Naga-Waukee Park, offering spectacular vistas from its boardwalks.
Planning your ride is straightforward, with the route often utilizing sections of the Lake Country Trail. Remember that a Waukesha County Parks & Land Use trail pass is required for cyclists aged 12 and older on these segments. Delafield, a convenient stop along the way, offers a bustling downtown with cafes and shops, while trailheads like the Fish Hatchery Sports Complex provide parking and restrooms.
This route isn't just about the scenery; it also carries a touch of history, often following the path of the old Milwaukee-Watertown Interurban Railway. Its connectivity is a major plus, linking to other networks like the Ice Age National Scenic Trail and the Glacial Drumlin State Trail for those looking to extend their cycling adventures beyond the estimated 2 hours and 43 minutes.
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Popular around Oconomowoc
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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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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This in a nice spot to take a break and take in the beautiful views of Pewaukee Lake.
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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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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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Nagawicka Lake is a great place for outdoor pursuits; you can boat, swim and fish here. The water covers an area of 981 acres.
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Extremely long barn unlike anything I have seen before with a lot of history.
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There are over 15 touring cycling routes around Oconomowoc, offering a variety of options for different skill levels and preferences. These routes are well-regarded by the komoot community.
Yes, Oconomowoc offers several easy touring cycling routes perfect for families. For instance, the Bike loop from Good Shepherd Methodist Church is a straightforward 9.5-mile (15.2 km) ride with modest elevation changes, making it very accessible.
The touring cycling routes around Oconomowoc are characterized by numerous lakes and gently rolling terrain. You'll find a mix of paved bike trails and quiet roads, with generally modest elevation changes, making the region accessible for recreational riders.
For those seeking a more challenging ride, Oconomowoc has several moderate routes. The Nagawicka Lake loop from Okauchee Lake, for example, is a 28.1-mile (45.3 km) route with more significant elevation gains, offering a good workout for experienced touring cyclists.
Many routes offer scenic views of the area's numerous lakes. You can cycle along the shores of Nagawicka Lake and Pewaukee Lake. Additionally, the Lake Country Trail and Glacial Drumlin State Trail are notable cycling paths in the region.
Yes, most of the touring cycling routes in Oconomowoc are designed as loops, allowing you to start and end at the same point. Examples include the Bike loop from Nagawaukee Park & Ride and the Pewaukee Lake loop from Nagawaukee Park & Ride.
The spring, summer, and fall months generally offer the most pleasant conditions for touring cycling in Oconomowoc, with comfortable temperatures and vibrant scenery. The region's modest elevations make it enjoyable throughout these seasons.
Many routes conveniently start from public access points like parks or designated parking areas. For example, the Bike loop from Nagawaukee Park & Ride begins directly from a park and ride facility, offering easy parking.
While many local roads and paths are freely accessible, some state trails, like sections of the Glacial Drumlin State Trail, may require a state trail pass. It's advisable to check the Wisconsin DNR website for current permit requirements for specific state trails.
The touring cycling routes in Oconomowoc are highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the beautiful lakeside landscapes, the mix of quiet roads and paved trails, and the accessibility of the routes for various skill levels.
For dedicated cycling paths, the Lake Country Trail and sections of the Glacial Drumlin State Trail offer excellent paved surfaces suitable for touring bicycles. Many routes also incorporate quiet local roads that are popular with cyclists.
The routes vary in length, from shorter rides like the Bike loop from Oconomowoc at 7.9 miles (12.7 km) taking about 45 minutes, to longer options such as the Nagawicka Lake loop from Okauchee Lake, which is 28.1 miles (45.3 km) and can take over 2 hours.


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