4.9
(18)
859
riders
41
rides
Road cycling around Greendale offers a variety of routes that traverse parklands, river corridors, and shoreline areas. The region features relatively flat terrain with gentle elevation changes, making it accessible for different skill levels. Routes often follow established trails like the Oak Leaf Trail and Root River Parkway, providing dedicated paths for cyclists. The landscape is characterized by urban green spaces, riverine environments, and proximity to larger bodies of water.
Last updated: May 21, 2026
46
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
27
riders
27.1km
01:25
90m
90m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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5.0
(1)
15
riders
106km
04:45
410m
410m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
18
riders
65.1km
02:57
190m
190m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
14
riders
64.1km
02:55
310m
310m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Greendale
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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North Wahl Avenue glides along the shore of Lake Michigan while passing Bradford Beach, North Point Lighthouse, and Lake Park. It's only a short distance but the views from this stretch of road are sure to be a highlight of your ride.
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Riding down South Shore Drive is a great way to take in the beautiful views of Downtown Milwaukee and the lake. There's a park and a number of restaurants and cafes to stop at if you'd like to stay a while.
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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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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.
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A beautiful path with expansive views of Lake Michigan. A perfect path to cycle on, on a still summers day.
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A great little pond to make a rest stop along your bike ride on the Oak Leaf trail There are usually people fishing on the shore to take a look at.
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Road cycling routes around Greendale are generally characterized by relatively flat terrain with gentle elevation changes. You'll find paths traversing parklands, river corridors, and shoreline areas, often following dedicated trails like the Oak Leaf Trail and Root River Parkway. The landscape features urban green spaces and riverine environments.
There are over 40 road cycling routes available around Greendale, offering a diverse range of options for different skill levels and preferences.
Yes, Greendale offers many routes suitable for beginners. Approximately 30 of the routes are rated as easy, providing smooth rides through green spaces. An example is the Oak Leaf Trail loop from Franklin, which is 16.8 miles long and primarily follows the dedicated Oak Leaf Trail.
While the region is known for its gentle terrain, there are longer, moderate routes that offer a good challenge for experienced cyclists. For instance, the Hoyt Park Footbridge – Lincoln Park loop from Milwaukee Airport is a substantial 66.6-mile (107.2 km) ride with over 1,300 feet (413 m) of elevation gain, providing a longer endurance test.
Yes, many road cycling routes in Greendale are designed as loops, making them convenient for starting and ending at the same point. Popular examples include the Grant Park Beach – Oak Leaf Trail — Shore line loop from Milwaukee Airport and the Highland Memorial Park – Root River Parkway loop from Truck Parking.
The road cycling routes in Greendale are highly rated by the komoot community, with an average score of 4.9 stars from over 10 reviews. Cyclists often praise the well-maintained parkway trails, scenic river routes, and extensive shoreline loops that offer varied and enjoyable rides.
Many routes offer scenic views and pass by interesting landmarks. You can explore areas like the Hank Aaron State Trail, ride past Highland Memorial Park, or enjoy views of Lake Evinrude. Some routes also provide a stunning View of Downtown Milwaukee from South Shore Drive.
Greendale's relatively flat terrain and dedicated trails make it ideal for family-friendly road cycling. Many of the easy routes, particularly those following the Oak Leaf Trail, are suitable for families looking for a relaxed ride through green spaces.
The best time for road cycling in Greendale is typically from spring through autumn, when the weather is mild and the trails are clear. The region's urban green spaces and parkways are particularly pleasant during these seasons.
While specific cafes are not listed for every route, many routes traverse urban green spaces and pass through or near communities where you can find various amenities, including cafes and restaurants, especially along the more populated sections of the Oak Leaf Trail and near park entrances.
For scenic views, consider routes that hug the shoreline or follow river corridors. The Grant Park Beach – Oak Leaf Trail — Shore line loop from Milwaukee Airport offers extensive shoreline views, while the Grant Park Beach – Oak Leaf Trail — Shore line loop from Mangan Woods also provides beautiful coastal scenery.
Given Greendale's proximity to Milwaukee and its urban green spaces, many road cycling trails, particularly those part of larger networks like the Oak Leaf Trail, are often accessible via public transport options in the wider metropolitan area. It's advisable to check local transit schedules and bike-on-bus/train policies for specific access points.


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