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Road cycling routes
United States
Wisconsin
Waukesha County

Pewaukee

The best road cycling routes around Pewaukee

4.6

(60)

764

riders

67

rides

Road cycling around Pewaukee offers a diverse landscape characterized by rolling hills, open farmland, and prominent lake views. The region, part of Wisconsin's Lake Country, features a mix of natural and semi-rural scenery. Cyclists can expect routes that traverse marshlands and patches of forests, with some sections providing direct views of Pewaukee Lake and Nagawicka Lake. Lapham Peak, though a hill under 200m, provides more challenging terrain with elevation gains.

Best road cycling routes around Pewaukee

  • The most popular road…

Last updated: June 28, 2026

47

riders

#1.

New Berlin Recreation Trail – Highland Memorial Park loop from Manhattan & Moreland

47.8km

02:02

150m

150m

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

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Moderate

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

Easy
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12

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

11

riders

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

Moderate
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Popular around Pewaukee

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Tips from the Community

David Howells
June 28, 2025, Hank Aaron Trail

This 15.6 mile shared used paved trail is named after the baseball legend Hank Aaron. It provides a continuous connection between American Family Field, home of the Milwaukee Brewers, and the Lake Michigan lakefront.

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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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As you cycle by Highland Memorial Park on the New Berlin Recreation Trail, you'll notice a peaceful and serene environment. This section of the trail offers a refreshing change with well-maintained grass and lush green trees, providing a picturesque backdrop to your ride. The tranquil atmosphere makes it a perfect spot to slow down and enjoy the scenery.

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The New Berlin Recreation Trail is a 7-mile paved path running east-west from New Berlin to Waukesha in the Milwaukee suburbs. Although it lacks trestles and tunnels, it’s popular among commuters for its convenience and speed, following power lines. Starting at Lincoln St., the trail heads east with a 3-mile stretch free of street crossings. It runs parallel to an active railroad, maintaining a safe distance. Highlights include a bike shop and cafes at Calhoun St., restrooms at Buena Park, and the scenic Gatewood Park further along.

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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 15.6 mile shared used paved trail is named after the baseball legend Hank Aaron. It provides a continuous connection between American Family Field, home of the Milwaukee Brewers, and the Lake Michigan lakefront.

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Frequently Asked Questions

What kind of terrain can I expect when road cycling around Pewaukee?

Pewaukee's landscape offers a diverse mix for road cyclists. You'll find routes winding through rolling hills and open farmland, characteristic of a classic Midwestern cycling experience. Many paths also provide scenic lakeside views of Pewaukee Lake and Nagawicka Lake, and some sections traverse marshlands and patches of forests. For those seeking more challenge, areas like Lapham Peak offer noticeable elevation gains.

Are there any challenging road cycling routes in Pewaukee?

Yes, while many routes are moderate or easy, some offer more challenging terrain. For instance, the area around Lapham Peak, formed by glacial activity, provides elevation gains that can test your climbing skills. A popular route that includes this area is the Lapham Peak loop from Village of Pewaukee, which is rated as moderate and covers nearly 50 km with significant elevation changes.

What natural features or landmarks can I see along the road cycling routes?

Road cycling routes in Pewaukee offer views of prominent natural features such as Pewaukee Lake and Nagawicka Lake. You'll also pass through marshlands, forests, and open farmland. Notable attractions nearby include Menomonee Park and the scenic Merton Millpond and Bark River, which is a great spot for nature observation.

Are there family-friendly road cycling routes in Pewaukee?

Yes, Pewaukee offers several routes suitable for families. The Lake Country Trail is particularly well-suited, being a paved, well-maintained path largely following an old railway. Its flat sections and scenic views make it ideal for cyclists of varying ages and abilities. Routes like the Nagawicka Lake loop from Meadowbrook Park & Ride are rated as easy and provide a pleasant experience.

Do I need a trail pass for road cycling on trails in Pewaukee?

Yes, for certain trails like the Lake Country Trail, which is part of the Wisconsin State Trail system, a Wisconsin State Trail Pass is typically required for cyclists aged 16 and older. It's always a good idea to check the latest regulations before you ride.

Where can I park my car when accessing road cycling routes in Pewaukee?

Several convenient parking options are available. The Landsberg Center, a well-equipped trailhead for the Lake Country Trail, offers public restrooms, drinking water, and bicycle racks. Many other routes also have designated parking areas, often at parks or trailheads, making access straightforward.

When is the best time of year to road cycle in Pewaukee?

The best time for road cycling in Pewaukee is generally during the spring, summer, and fall months. These seasons offer pleasant temperatures and vibrant scenery, from blooming spring flowers to lush summer greenery and colorful autumn foliage. Winter cycling is possible but requires appropriate gear and caution due to colder temperatures and potential snow or ice.

Are there any facilities like restrooms or water along the road cycling trails?

Yes, dedicated facilities are available on some key trails. The Landsberg Center, located along the Lake Country Trail, is an excellent resource, providing public restrooms, drinking water, a bottle-filling station, and even a bicycle self-service station. Other parks and trailheads may also offer amenities.

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

The road cycling experience in Pewaukee is highly rated by the komoot community, with an average score of 4.7 stars from over 50 reviews. Cyclists often praise the region's diverse scenery, including rolling hills, open farmland, and beautiful lakeside views. The well-maintained trails and the variety of routes catering to different skill levels are also frequently highlighted.

Are there any circular road cycling routes in Pewaukee?

Yes, Pewaukee offers several excellent circular routes. Popular options include the Pewaukee Lake loop from City of Pewaukee, which provides extensive lake views, and the Nagawicka Lake loop from Village of Pewaukee, leading through lakeside areas and varied terrain. These loops allow you to start and end your ride in the same location.

Are there places to eat or stay near the road cycling routes in Pewaukee?

Pewaukee is a cyclist-friendly area with amenities close to its routes. You'll find local cafes, pubs, and accommodation options in the towns and villages along or near the trails. VéloCity Cycling, a local bike shop, even features "The Handlebar," a cyclist-friendly meeting place with views of Pewaukee Lake, making it a great spot to refuel.

What is the longest road cycling route available in Pewaukee?

Among the featured routes, the Pewaukee Lake loop from City of Pewaukee is a substantial option, covering approximately 75.3 km (46.8 miles). This moderate route offers extensive views of Pewaukee Lake and utilizes paved roads and cycleways, making for a rewarding long ride.

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