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.

Sign up for free
5.0
(1)
17
riders
114km
05:03
430m
440m
Hard road ride. Very 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.
5.0
(1)
14
riders
20.8km
00:51
90m
90m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy 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 Greendale
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
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
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.
0
0
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.
0
0
A beautiful path with expansive views of Lake Michigan. A perfect path to cycle on, on a still summers day.
0
0
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.
0
0
The Abandoned Ladish Sand Pit is often filled in with water and right off of the Oak Creek Trail. Oak Creek runs right behind it, making this spot a nice area to keep an eye out for birds and other wildlife.
0
0
Grant Park Drive runs along the coast but is separated from Grant Park Beach by a strip of woodland. There are some trails through the woods so you can access the beach from a number of different places, but the best option is to use the Oak Creak parking lot near Ferch's Beachside Grille. There are plenty of services here such as a playground and café, and you can walk right onto the beach.
0
0
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.


Browse the best Road cycling routes in other regions.