THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
A compact, guided weekend ride from Chicago to Milwaukee that combines lakefront cycling, coastal towns like Kenosha, and Milwaukee’s brewery and museum scene. Expect 74.6 miles over two days on mostly paved roads with support and one hotel night included.
A compact, guided weekend ride from Chicago to Milwaukee that combines lakefront cycling, coastal towns like Kenosha, and Milwaukee’s brewery and museum scene. Expect 74.6 miles over two days on mostly paved roads with support and one hotel night included.
Book with Green Path Pedals
Book directly with Green Path Pedals for the best rates and real-time scheduling.
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Operated by Green Path Pedals · Milwaukee, Wisconsin
You roll out at 7 a.m., tires kissing pavement as the lake yawns to your right and a cold south wind dares you to keep pace. The first miles slice through quiet suburbs and separated bike paths; the Bahāʾī House of Worship and limestone homes in Wilmette briefly shadow the road before the route opens toward Kenosha and the long ribbon of Lake Michigan.
moderate.
Approx. 34 hours (weekend).
Should be comfortable riding 35–45 miles in a day at a steady pace with short breaks; regular cyclists will find this accessible.
Yes—participants use their own bikes; organizers provide a pump and support vehicle but not rental bikes.
A moderate fitness level is required: plan to ride up to ~75 miles over two days with steady group pacing and scheduled breaks.
Meals listed in the itinerary (breakfast, brunch, lunches, dinner), one hotel night in Milwaukee, route planning, and a support vehicle are included.
Tours can be canceled for bad weather—check the operator’s 24-hour cancellation policy for refunds and reschedule options.
The route traces Great Lakes shoreline shaped by glaciers and connects Chicago’s lakeshore neighborhoods to Milwaukee’s brewing legacy and riverfront redevelopment.
Stick to established paths near dunes and beaches, pack out all trash, and support local trail maintenance groups to reduce erosion and habitat disturbance.
Green Path Pedals operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
Book with Green Path Pedals
Book directly with Green Path Pedals for the best rates and real-time scheduling.
Reserve Now