Lake Michigan Lollipop

A stunning ride along Lake Michigan's shoreline and through deep forests.

Road Biking Easy

48 km
330 m
330 m
2-3 hrs
Low Point
178 m
High Point
219 m
Lake Michigan Lollipop Map

While to an outsider Milwaukee might not spring to mind as a city with any outdoor activities, as soon as you start exploring this small metropolis you’ll realize that the city planners have placed a premium on green space and outdoor access despite the area’s industrial past. In fact, the Milwaukee County Parks system—through which most of this route runs—received a 2009 NRPA Gold Medal Award for the best-managed park system in the nation. Milwaukee has also been recognized as a Tree City USA for 30 years running, as of 2009 (the latest year their website provides information for), along with a bronze-level Bicycle Friendly Community designation. All things considered, if you live in or are visiting Milwaukee, it’s a pretty great place to ride a road bike!


The route mapped here makes use of Milwaukee’s most excellent natural resource: the expansive Lake Michigan. The stick of this lollipop route runs along the shores of the lake, sometimes immediately on the water, and at other times winding through the beautiful parks that have been protected along the shoreline. Hearing the waves crashing against the shore, feeling the wind off the water, and listening to the cry of the seagulls may remind you of the ocean—minus the smell of saltwater.

The loop on this lollipop runs deeper into the city, but still manages to mostly follow protected bike paths along river greenways as it heads further inland. In order to complete the loop, riders will have to do some open road pedaling, but this route has been designed to avoid busy streets as much as possible. You’ll quickly return to the safety and serenity of the bike paths.

While the lake may take the prize as the most outstanding feature of this route, the long expanse of parks and open spaces through which this route runs is truly impressive for a city of Milwaukee’s size and industrial past. It seems that their NRPA Gold Medal Award was well-deserved! While pedaling through the deep woods of Grant Park, you could be forgiven for thinking you’re riding through the rolling countryside in Germany or Belgium on a narrow paved highway.

This route is a true gem—be sure to put it on your Milwaukee road biking hit list!





1 out of 4

Close to help in case of emergency.

Best time to visit

between May and October