4.7
(67)
1,189
riders
103
rides
Road cycling in Waukesha County offers diverse landscapes, characterized by glacial hills, numerous kettle lakes, and extensive woodlands. The region features a network of paved trails, many of which follow former railway lines, providing varied terrain for cyclists. These routes traverse agricultural areas, natural parks, and scenic lakefronts, making the county a notable destination for outdoor activities. The topography includes gentle inclines and flatter sections, suitable for a range of cycling preferences.
Last updated: April 24, 2026
71
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
(1)
27
riders
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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5.0
(1)
7
riders
68.3km
02:53
320m
320m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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.
4
riders
41.4km
01:49
140m
140m
Easy road ride. Great for any fitness level. 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.
61
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
53
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
47
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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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.
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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 Hank Aaron State Trail runs alongside the Menomonee River, and at this point, you can access a viewpoint with nice views of the river and the small greenbelt surrounding it.
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Situated on the city's beautiful waterfront, The Milwaukee Art Museum is the largest in the state. It features a collection of nearly 32,000 artworks across four floors, including modern and contemporary pieces, as well as notable architecture. The collection spans from ancient times to the present and includes European and American paintings, sculptures, prints, drawings, decorative arts, photographs, and folk art.
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General MacArthur was the top cadet of West Point's 1903 class. This sculpture honors him for his leadership in the Pacific during World War II. MacArthur, his father, and his grandfather were all Milwaukee residents. His last visit to the city was on April 27, 1951, when he received an honorary degree from Marquette University.
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The Milwaukee Art Museum is known for its striking architecture, especially the Burke Brise Soleil, which opens and closes like wings. Don’t miss the stunning views of Lake Michigan from the museum’s café. With rotating exhibitions and an impressive permanent collection, it’s worth taking your time to explore both the art and the building itself.
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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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Waukesha County offers a wide selection of road cycling routes, with over 100 options available. These routes cater to various skill levels, from easy rides to more moderate challenges.
The road cycling routes in Waukesha County are highly rated by the komoot community, with an average score of 4.8 stars from over 70 reviews. Cyclists often praise the diverse landscapes, including glacial hills, kettle lakes, and extensive woodlands, as well as the well-maintained paved trail networks.
Yes, Waukesha County has many easy road cycling routes perfect for beginners and families. For instance, the Glacial Drumlin State Trail is an easy 30-mile path showcasing picturesque landscapes of farmland, woodlands, and wetlands. Another great option is the New Berlin Recreation Trail – Highland Memorial Park loop from Waukesha, which is also rated as easy.
While many routes are easy, Waukesha County also offers moderate options for those seeking a greater challenge. Routes like the Bugline and Lake Country Trail Loop, a 42.5-mile trail leading through former quarry areas and past lakes, provide varied terrain and longer distances. The Lake Country Trail Loop is another moderate option, covering over 30 miles.
Yes, many road cycling routes in Waukesha County are designed as loops, offering convenient starting and ending points. Examples include the Glacial Drumlin and Lake Country Trail Loop, the Lake Country Trail Loop, and the New Berlin Trail Loop.
Waukesha County's road cycling routes traverse diverse landscapes shaped by glaciers. You'll encounter picturesque farmland, extensive woodlands, and wetlands, particularly along trails like the Glacial Drumlin State Trail. The region also features unique glacial hills and numerous kettle lakes, offering varied and scenic views.
Absolutely. The Lake Country Trail, for example, offers scenic views of Pewaukee Lake and Nagawicka Lake. You can experience these views on routes such as the Lake Country Trail itself or the Glacial Drumlin and Lake Country Trail Loop. Naga-Waukee Park, accessible from the Lake Country Trail, also provides access to these beautiful lakes.
Along the road cycling routes, you can explore several natural attractions. The Kettle Moraine Area, with its glacial hills and lakes, is a prominent feature. You can also visit parks like Menomonee Park, which features a swimming lake, or enjoy views of the Kettle Moraine State Forest. Many trails also run alongside the Fox River, providing scenic river views.
Yes, several parks and natural areas are easily accessible by bike. The Fox River Trail winds through the City of Waukesha, starting from Frame Park and extending to Fox River County Park. Other notable parks include Menomonee Park, which is part of the Menomonee Park – Merton Millpond and Bark River loop from Lovers Lane Estates route, and the Retzer Nature Center, which offers hiking and biking trails.
The spring, summer, and fall months generally offer the best conditions for road cycling in Waukesha County. During these seasons, the weather is pleasant, and the natural landscapes are vibrant. While some trails may be accessible in winter, conditions can vary, and specific segments might be compacted dirt rather than paved, so it's best to check local conditions.
Many of Waukesha County's paved trails are free to access without an annual membership or daily permit. For detailed information on specific trails, including access points and any potential permit requirements, you can visit the official Waukesha County Parks and Land Use website: waukeshacounty.gov.
Yes, the New Berlin Recreation Trail is known for its convenience and speed, featuring a 3-mile stretch that is largely free of street crossings. This makes it a popular choice for uninterrupted rides. You can explore this on routes like the New Berlin Trail Loop.
Several notable trails in Waukesha County follow former railway lines, providing relatively flat and scenic routes. The Lake Country Trail, for instance, is a 15-mile paved trail that follows a former interurban railway. The Glacial Drumlin State Trail also utilizes a former rail corridor, offering a long, continuous path through varied landscapes.


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