1.
Veterans Park Lagoon – Hoyt Park Footbridge loop from Goethe-Schiller Monument
48.8km
02:01
150m
150m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
View route
The best road cycling routes around Wauwatosa
By Fede from komoot
·
Updated June 2, 2026
If you've ever tried to plan road cycling around Wauwatosa, you know how overwhelming the options can be. With so many trails and parkways, it's tough to figure out which routes are genuinely worth your time and effort, and which are just filler. You want the good stuff, the rides that make your legs happy and your spirit soar, without endless guesswork.
That's where we come in. Our komoot community has meticulously mapped, ridden, and reviewed countless routes around Wauwatosa. We've sifted through the data to bring you a curated shortlist of the best road cycling routes, saving you the hassle and pointing you straight to the experiences that truly deliver.
Road cycling in Wauwatosa is all about its fantastic, interconnected network of paved, multi-use trails, especially the extensive Oak Leaf Trail system. You'll find generally flat terrain, particularly along the scenic river parkways, though some urban sections offer moderate slopes to keep things interesting. This means there are options for all ability levels, from easy, flat spins to routes with a bit more urban incline. The numerous parks, like Hart Park and Hoyt Park along the Menomonee River, provide beautiful green spaces and easy access points to the trail system.
If you only do one ride, we'd point you to the Hank Aaron State Trail – Hoyt Park Footbridge loop from Wauwatosa. At 22.4 miles (36.1 km) with 624 feet (190 m) of elevation gain, it's an easy route that connects you to key parts of the city's trail network. For a slightly longer adventure, the Veterans Park Lagoon – Lincoln Park loop from Bob Uecker - "Mr. Baseball" is a moderate 31.2 miles (50.2 km) ride that traverses various parks and segments of the Oak Leaf Trail, perfect for exploring more of Wauwatosa's green spaces. Dive in and discover your next favorite ride with komoot!
If you only do 3 of these routes
Compare these routes at a glance
Trail | Distance | Elevation | Difficulty |
|---|---|---|---|
| Veterans Park Lagoon – Hoyt Park Footbridge loop from Goethe-Schiller Monument | 48.8 km | 150 m | Moderate |
| Hoyt Park Footbridge – Root River Parkway loop from Wauwatosa | 51.9 km | 160 m | Moderate |
| Hoyt Park Footbridge loop from Goethe-Schiller Monument | 25.4 km | 130 m | Easy |
| Hoyt Park Footbridge – Pewaukee Lake loop from West Allis | 76.6 km | 500 m | Moderate |
| Highland Memorial Park – New Berlin Recreation Trail loop from Medical College of Wisconsin | 79.4 km | 460 m | Moderate |
| Hank Aaron Trail – Hoyt Park Footbridge loop from Wauwatosa | 38.4 km | 190 m | Easy |
| Hoyt Park Footbridge loop from Wauwatosa | 36.1 km | 240 m | Easy |
| Hoyt Park Footbridge – Lakeshore State Park loop from University of Wisconsin-Milwaukee | 61.8 km | 240 m | Moderate |
| Highland Woods – Colectivo Coffee Mequon loop from Annunciation Greek Orthodox Church | 47.3 km | 130 m | Easy |
| Hank Aaron Trail – Hank Aaron State Trail loop from Wauwatosa | 26.7 km | 160 m | Easy |
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Hoyt Park Footbridge – Root River Parkway loop from Wauwatosa
51.9km
02:45
160m
160m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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3.
Hoyt Park Footbridge loop from Goethe-Schiller Monument
25.4km
01:07
130m
130m
Easy road ride. Mostly well-paved surfaces and easy to ride.
View route
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4.
Hoyt Park Footbridge – Pewaukee Lake loop from West Allis
76.6km
03:27
500m
500m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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5.
Highland Memorial Park – New Berlin Recreation Trail loop from Medical College of Wisconsin
79.4km
03:21
460m
460m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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6.
Hank Aaron Trail – Hoyt Park Footbridge loop from Wauwatosa
38.4km
01:41
190m
190m
Easy road ride. Mostly well-paved surfaces and easy to ride.
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7.
Hoyt Park Footbridge loop from Wauwatosa
36.1km
01:36
240m
250m
Easy road ride. Mostly well-paved surfaces and easy to ride.
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8.
Hoyt Park Footbridge – Lakeshore State Park loop from University of Wisconsin-Milwaukee
61.8km
02:47
240m
240m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
View route
9.
Highland Woods – Colectivo Coffee Mequon loop from Annunciation Greek Orthodox Church
47.3km
01:51
130m
130m
Easy road ride. Mostly well-paved surfaces and easy to ride.
View route
10.
Hank Aaron Trail – Hank Aaron State Trail loop from Wauwatosa
26.7km
01:08
160m
160m
Easy road ride. Mostly well-paved surfaces and easy to ride.
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Tips from the Community
Andrus
May 25, 2025, Milwaukee Riverwalk
The 104-mile Milwaukee River flows through eastern Wisconsin before emptying into Lake Michigan. Here in Milwaukee you can enjoy a run along the Riverwalk while passing through a few of the parks that dot its banks.
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Sue
January 25, 2025, Milwaukee Art Museum
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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Andrus
January 10, 2025, Hoyt Park Footbridge
The Hoyt Park Footbridge dates back to the 1939 and the New Deal. The CCC built countless projects across the country in order to drive recovery from the Great Depression and this beautiful bridge is part of that legacy.
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oliviakellis
June 25, 2024, Sanctuary Woods
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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oliviakellis
June 25, 2024, Highland Memorial Park
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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oliviakellis
June 25, 2024, New Berlin Recreation Trail
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 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.
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oliviakellis
June 24, 2024, Glacial Drumlin State Trail
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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Frequently Asked Questions
How many road cycling routes are available in Wauwatosa?
Wauwatosa features over 25 road cycling routes, providing a wide range of options for cyclists. These routes are highly rated by the komoot community, with an average score of 4.6 stars.
What are the primary road cycling trails in Wauwatosa?
The cornerstone of road cycling in Wauwatosa is the Oak Leaf Trail, an extensive paved, multi-use system spanning over 135 miles throughout Milwaukee County. The Hank Aaron State Trail also crosses Milwaukee County and connects to Wauwatosa, offering another excellent paved route.
What kind of terrain can I expect on Wauwatosa's road cycling routes?
The terrain in Wauwatosa is generally flat, especially along river parkways like the Menomonee River Parkway. However, some urban sections of the Oak Leaf Trail do include moderate slopes, offering a varied experience for cyclists.
Are there road cycling routes suitable for different skill levels?
Yes, Wauwatosa offers routes for various skill levels. You'll find 15 easy routes, such as the Dragonfly Pond – Hoyt Park Footbridge loop from Inglewood, which is 21.6 miles long. There are also 10 moderate routes, like the Lincoln Park – Hoyt Park Footbridge loop from Valley Forge, which covers 31.4 miles.
What can I see along the road cycling routes in Wauwatosa?
Many routes traverse Wauwatosa's diverse parks and natural areas. You can pass by Hoyt Park Footbridge, explore the expansive County Grounds Park with its rolling hills and Sanctuary Woods, or enjoy the tranquil Menomonee River Parkway. Some routes also connect to attractions like the Milwaukee County Zoo via the Hank Aaron State Trail.
Are there any interesting historical sites or natural features to explore?
Absolutely. County Grounds Park, for instance, contains remnants of historic infrastructure from an 1800s asylum, adding a unique historical dimension. Hartung Park is known for fossils of trilobites found within its grounds, and Jacobus Park features a mile-long nature trail designated as a National Recreation Trail.
What is the best time of year for road cycling in Wauwatosa?
While cycling is enjoyable throughout the warmer months, many users particularly enjoy riding in July and August. The extensive paved trail systems are well-maintained, making them accessible for much of the year, though conditions can vary seasonally.
Are the road cycling trails in Wauwatosa family-friendly?
Yes, many segments of the Oak Leaf Trail and the Hank Aaron State Trail are considered family-friendly, offering mostly smooth, paved surfaces. Routes like the Dragonfly Pond – Hoyt Park Footbridge loop from Inglewood are classified as easy, making them suitable for families.
Where can I park to access road cycling routes in Wauwatosa?
The extensive Oak Leaf Trail system provides dozens of access points within Wauwatosa and surrounding communities, often with associated parking. Parks like Hart Park, Hoyt Park, and Hansen Park serve as convenient entry points to the trail network.
Are there amenities like cafes or pubs along the routes?
Wauwatosa's urban setting means that many routes pass through or near areas with amenities. The trails connect various parks and communities, increasing the likelihood of finding cafes, pubs, and other services nearby, especially in downtown Wauwatosa or along the Menomonee River Parkway.
Are there any loop road cycling routes in Wauwatosa?
Yes, many of the road cycling routes in Wauwatosa are designed as loops, allowing you to start and end in the same location. Examples include the Oak Leaf Trail – Hoyt Park Footbridge loop from Historic Heights and the Sanctuary Woods – Hoyt Park Footbridge loop from Historic Heights.
What do other road cyclists enjoy most about cycling in Wauwatosa?
The komoot community highly rates road cycling in Wauwatosa, with an average score of 4.6 stars. Cyclists frequently praise the extensive and well-maintained paved trail systems, particularly the Oak Leaf Trail, and the ability to connect various parks and green spaces within an urban environment.
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