Chiwaukee Prairie Ramble is a 20.7 mile moderately trafficked loop trail located near Pleasant Prairie, Wisconsin that features a lake and is good for all skill levels. The trail offers a number of activity options and is best used from March until October.

20.7 miles
239 feet

kid friendly


nature trips

paddle sports

road biking

trail running




wild flowers


Escape during a rural tour of Pleasant Prairie, WI. Originally inhabited by pre-pioneer indians, this area offers something besides it's proximity to Chicago and Milwaukee. The settlers that followed found tranquil living in the prairies along the Lake Michigan shoreline. This area became known as Chiwaukee, due to it's equal distance between Chicago and Milwaukee, before it became the Village of Pleasant Prairie later that century. Now a bedroom community for commuters to workplaces in Chicago and Milwaukee, modern day settlers call this peaceful spot home. On the fringe of the more urban Kenosha, lies a perfect escape for a ride amongst cornfields and beaches. You'll soon forget you're only an hour from Chicago or Milwaukee via I-94. The well equipped Prairie Springs Park, literally only 60-seconds from I-94, offers the perfect spot to start and end your road tour. Here you can find parking and plenty of things to do fill out the day after your tour. Or just relax your feet in the cool waters of Lake Andrea. Its proximity to Chicago and Milwaukee, Prairie Springs Park, and it's more rural setting make this area the choice for multiple triathlons every year. You'll be biking some of the same areas, but at a much more leisurely pace.