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Greendale

The best road cycling routes around Greendale

By Fede from komoot

·

Updated June 4, 2026

If you have ever tried to plan road cycling around Greendale, you know how overwhelming the options can be. With so many trails and routes, it is hard to tell which ones are genuinely worth your time and effort, and which are just filler. That is where we come in. Our komoot community has mapped, ridden, and reviewed countless routes here, so we have done the legwork to bring you a curated shortlist of the very best, saving you the guesswork.

Road cycling around Greendale offers a unique blend of urban green spaces and scenic riverine environments. The area is characterized by its relatively flat terrain and gentle elevation changes, making it accessible for a wide range of skill levels. You will find an extensive network of established trails, particularly the popular Oak Leaf Trail and Root River Parkway, which form the backbone of many routes. This "Greenbelt town" design means you are often cycling through lush parklands and along waterways, providing a pleasant escape from city bustle.

If you only do one ride, make it the Grant Park Beach – Oak Leaf Trail — Shore line loop from Milwaukee Airport. At 50.3 miles (80.9 km), this moderate route is our community's most popular for good reason, offering extensive shoreline views and connecting various park areas. For something a bit shorter and easier, the Oak Leaf Trail – Root River Parkway loop from Franklin is a local favorite, an easy 16.8 miles (27.1 km) that provides a smooth ride through green spaces. With more than 600 road cyclists already exploring Greendale with komoot, you are in good company.

If you only do 3 of these routes

  1. 1

    Grant Park Beach – Oak Leaf Trail — Shore line loop from Milwaukee Airport
  2. 2

    Oak Leaf Trail – Root River Parkway loop from Franklin
  3. 3

    Root River Parkway – Highland Memorial Park loop from Milwaukee Airport

Compare these routes at a glance

Trail

Distance

Elevation

Difficulty

Grant Park Beach – Oak Leaf Trail — Shore line loop from Milwaukee Airport

82.4 km

320 m

Moderate

Oak Leaf Trail – Root River Parkway loop from Franklin

27.1 km

90 m

Easy

Root River Parkway – Highland Memorial Park loop from Milwaukee Airport

65.1 km

190 m

Moderate

Oak Leaf Trail – Root River Parkway loop from Truck Parking

21.6 km

70 m

Easy

1.

Grant Park Beach – Oak Leaf Trail — Shore line loop from Milwaukee Airport

82.4km

04:01

320m

320m

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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2.

Oak Leaf Trail – Root River Parkway loop from Franklin

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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Tips from the Community

Martin
August 20, 2026, Oak Leaf Trail Winds Through Milwaukee

The Oak Leaf Trail winds through Milwaukee and its neighborhoods, creating a green band throughout the area. The great portion of these are paved and at the East Fort Hill Avenue, the trail changes to a very nice smooth crushed limestone path. A great pleasure to drive but would recommend tyre width of =>28mm.

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Oak Leaf Trail runs along the Milwaukee Lake Michigan Coast providing magnificent views of Lake Michigan and the Milwaukee Skyline. The paths themselves are on itself is a bit bumpy in some places due to roots pushing up the asphalt. The parc is a nicely shaded place, giving a bit of relief from the hot summer sun. The entire path from beginning to end is asphalted and is much smoother than the street running parallel to the cycleway. If one is here just to enjoy the sights, the cycleway is a good choice, if one wishes to make a lot of time, I suggest staying on the road which has very, very little traffic, I would in any event recommend tyres> 28mm width.

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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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A beautiful path with expansive views of Lake Michigan. A perfect path to cycle on, on a still summers day.

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Alex
January 29, 2024, Oak Leaf Trail

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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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.

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Frequently Asked Questions

What kind of terrain can I expect on road cycling routes in Greendale?

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.

How many road cycling routes are available around Greendale?

There are over 40 road cycling routes available around Greendale, offering a diverse range of options for different skill levels and preferences.

Are there road cycling routes suitable for beginners in Greendale?

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.

Are there challenging road cycling routes for experienced cyclists in Greendale?

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.

Are there many loop trails for road cycling in Greendale?

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.

What do other road cyclists enjoy the most about road cycling in Greendale?

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.

What can I see along the road cycling routes in Greendale?

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.

Are there any family-friendly road cycling routes in Greendale?

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.

When is the best time of year for road cycling in Greendale?

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.

Are there cafes or places to stop for refreshments along the road cycling routes?

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.

What are some of the most scenic road cycling routes in Greendale?

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.

Is public transport accessible to the road cycling trails in Greendale?

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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