The best road cycling routes around Wauwatosa
4.8
(9)
544
riders
27
rides
Road cycling around Wauwatosa is characterized by an extensive network of paved, multi-use trails, primarily the Oak Leaf Trail system. The region features generally flat terrain, particularly along river parkways, though some urban sections include moderate slopes. Numerous parks, such as Hart Park and Hoyt Park along the Menomonee River, provide green spaces and access points to the trail system. This interconnected network offers varied routes for road cyclists.
Best road cycling routes around Wauwatosa
- The most popular road cycling route is Dragonfly Pond – Hoyt Park Footbridge loop from Inglewood, a 21.6 miles (34.8 km) trail that takes 1 hour 24 minutes to complete. This easy route connects to Hoyt Park, offering views along the Menomonee River.
- Another top favourite among local road cyclists is Lincoln Park – Hoyt Park Footbridge loop from Valley Forge, a moderate 31.4 miles (50.5 km) path. This route traverses various parks and segments of the Oak Leaf Trail, providing a longer ride through Wauwatosa's green spaces.
- Local road cyclists also love the Oak Leaf Trail – Hoyt Park Footbridge loop from Historic Heights, a 31.3 miles (50.4 km) trail leading through the extensive Oak Leaf Trail system, often completed in about 2 hours 28 minutes.
- Road cycling around Wauwatosa is defined by its extensive paved trail systems like the Oak Leaf Trail, the Menomonee River parkways, and numerous urban parks. The network offers options for different ability levels, from easy, flat sections to routes with moderate urban inclines.
- The routes in Wauwatosa are highly rated by the komoot community with an average score of 4.6 stars from over 10 reviews. More than 400 road cyclists have used komoot to explore Wauwatosa's varied terrain.
Last updated: May 18, 2026
5.0
(1)
69
riders
36.1km
01:28
190m
190m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(3)
49
riders
50.2km
02:04
170m
170m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Sign up for free
4.5
(2)
50
riders
52.5km
02:48
160m
160m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
56
riders
25.4km
01:07
130m
130m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
54
riders
47.9km
02:36
180m
180m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Login or Signup
Popular around Wauwatosa
Tips from the Community
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.
0
0
This small pond is located in Three Bridges Park. It’s an easy short detour while cycling the Hank Aaron State Trail, offering a nice spot to take a break by the water.
0
0
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.
1
0
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.
0
0
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.
1
0
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.
0
0
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.
0
0
Veterans Park Lagoon is a 14-acre reservoir within the greater Veterans Park. Some paved paths circle around the water, and there is plenty of green space and picnic areas.
0
0
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.
Most popular attractions around Wauwatosa
Get inspired with the komoot mobile app
Explore more
Browse the best Road cycling routes in other regions.
