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Routes
Road cycling routes
United States
Wisconsin
Waukesha County

Waukesha

The best road cycling routes around Waukesha

255

riders

20

rides

Road cycling around Waukesha offers diverse terrain shaped by glacial history, featuring rolling hills, extensive trail networks, and scenic lake views. The region's landscape includes the distinctive Kettle Moraine, providing varied topography for cyclists. Numerous parks and greenways preserve open spaces, connecting natural environments suitable for road cycling. This combination of natural features and dedicated infrastructure creates an appealing environment for outdoor activities.

Best road cycling routes around Waukesha

  • The most popular road cycling route is New Berlin Trail Loop

Last updated: May 10, 2026

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riders

#1.

New Berlin Trail Loop

41.4km

01:49

140m

140m

Easy 25.7-mile road cycling loop on the New Berlin Trail, featuring paved paths, mixed scenery, and minimal elevation gain.

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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

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

Easy

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

Moderate
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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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Sanctuary Woods, nestled within the Wisconsin Medical College campus, holds the remnants of Milwaukee's first mental hospital. As you cycle through, you'll encounter aged sidewalks and paths that wind through deteriorating pavilions and scenic vistas. During the mid-20th century, this area housed about 6,000 individuals with mental illnesses. Built in the late 19th century, the now-abandoned facilities provide a poignant look into the area's history, offering a quiet, reflective atmosphere amidst the greenery.

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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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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 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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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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The Lapham Peak Observation Tower is located in the Kettle Moraine State Forest - Lapham Peak Unit and surrounded by multiple nice hiking trails. The 45-foot tower provides stunning views of the surrounding forest!

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Frequently Asked Questions

How many road cycling routes are available around Waukesha?

Waukesha offers a wide variety of road cycling routes. You can find nearly 20 routes, with options ranging from easy, paved paths to more moderate rides with varied elevations.

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

The terrain around Waukesha is largely shaped by its glacial history, featuring rolling hills, extensive trail networks, and scenic lake views. You'll encounter the distinctive Kettle Moraine landscape, providing varied topography that keeps rides interesting without being overly strenuous for all fitness levels.

Are there road cycling routes suitable for beginners in Waukesha?

Yes, Waukesha has several easy road cycling routes perfect for beginners. The New Berlin Trail Loop is a well-maintained paved path, and the Glacial Drumlin State Trail loop from University of Wisconsin-Milwaukee at Waukesha also offers an easy ride showcasing diverse Wisconsin scenery.

Where can I find longer road cycling routes in Waukesha?

For longer rides, many trails in Waukesha are interconnected, allowing you to combine them for extended journeys. Routes like the Highland Memorial Park – Hank Aaron State Trail loop from University of Wisconsin-Milwaukee at Waukesha offer moderate distances, utilizing multiple trail systems.

What are the most scenic road cycling routes in Waukesha?

Many routes offer beautiful scenery. The Lake Country Trail provides scenic lake views, while the Glacial Drumlin State Trail showcases diverse Wisconsin landscapes and glacial features. The New Berlin Recreation Trail – Highland Memorial Park loop from Waukesha also leads through serene environments with lush greenery.

What natural attractions can I see while road cycling in Waukesha?

While cycling, you can experience the unique glacial features of the Kettle Moraine, tranquil lakes like Nagawicka Lake, and extensive greenways. The Fox River Trail offers a scenic path alongside the Fox River, and areas like Retzer Nature Center provide diverse habitats to explore.

Are there any historical or cultural landmarks along the road cycling routes?

Yes, you can encounter several points of interest. The Highland Memorial Park is featured on some routes, offering a peaceful environment. Additionally, the Lapham Peak Observation Tower, accessible via routes like the Glacial Drumlin State Trail – Lapham Peak Observation Tower loop from Carroll University, provides panoramic views of the surrounding landscape.

Are there family-friendly road cycling options in Waukesha?

Absolutely. Many of Waukesha's trails, particularly the paved and relatively flat sections of the Glacial Drumlin State Trail and the New Berlin Recreation Trail, are excellent for families. These routes offer a safe and enjoyable experience for riders of all ages.

Can I find circular road cycling routes in Waukesha?

Yes, Waukesha's interconnected trail systems make it easy to find or create circular routes. Loops such as the New Berlin Trail Loop and the Glacial Drumlin State Trail loop from University of Wisconsin-Milwaukee at Waukesha are popular choices, allowing you to start and end at the same point.

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

The spring, summer, and fall months generally offer the most pleasant conditions for road cycling in Waukesha. The vibrant foliage in autumn and the lush greenery of spring and summer provide beautiful backdrops for your rides. Always check local weather conditions before heading out.

Where can I find parking for road cycling trails in Waukesha?

Many of Waukesha's parks and trailheads offer designated parking areas. For instance, Frame Park in downtown Waukesha provides convenient access to the Fox River Trail, and various access points along state trails like the Glacial Drumlin often have parking facilities. It's advisable to check specific trail access points for parking details.

Are there road cycling routes that offer amenities like cafes or rest stops?

While specific cafes are not listed for every route, many of Waukesha's trails pass through or near towns and communities where you can find amenities. The Fox River Trail, for example, runs through downtown Waukesha, offering access to various shops and eateries. Planning your route through these areas can provide convenient rest stops.

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