I noticed a post a few weeks back regarding Chicago’s stated ambition to be the best big city in America for cycling. I just love the message there, and thought it made sense to share with my cycling friends on Facebook. There was some immediate snark from a few non-cycling friends (not surprising), but in general everyone is excited to see big plans come together.

While sharing the post, I noticed someone had left this comment:

I've always been interested in finding a bike route from Milwaukee to Chicago.

To which I thought “YES, I can help you”, since I’ve made the trip up a few times. Here are your options:

Option 1: Bike paths

There are a great series of connected bike paths nearly all the way up to Milwaukee. Google Maps does a great job with directions (see route). In summary, you’ll hook onto the North Shore Channel Trail that starts on the NW edge of the city. This will take you through a few suburbs until you hit Highland Park, at which point you’ll make a few turns and then jump on the Green Bay Trail. The Green Bay Trail will lead you up to the Robert McClory Bike Path, which takes you all the way up to Kenosha. You’ll then follow the County Bike Trail through Racine, and finally end up about 5-10 miles shy of Milwaukee. You’ll ride in on open roads with extra-wide shoulders from there, a truly nice touch.

This is a fun ride to do with friends. Some friends and I rode up to Milwaukee (and then back the next day) in July of 2011 and had a great time.

Option 2: Open road

I know it sounds too simple to be true, but you can follow the Lake Michigan “Circle Tour” signs all the way up to Milwaukee (really).

Lake Michigan Circle Tour - These signs will help guide your way

They appear frequently and mark the route around the lake, so you can’t go wrong following them.

I chose this option in July 2012 and really enjoyed it. You can move a lot faster on the open road and you get to see a lot of great views while riding along the lake. I tracked the ride with my Garmin and posted it to Strava if you’re curious:

Which ride is right for you?

I think this really depends on what your goals and level of riding experience are. If you’re not comfortable riding on the road alongside fast moving cars then definitely take the paths. On the other hand, if you do a lot of group riding (which usually follows busy streets) the paths will drive you nuts because they slow you down.

There’s also a post on ‘the chainlink’ with helpful notes and commentary.

To anyone venturing up their this spring, summer, or fall - have fun! Let me know if you have any questions.

Photo credit: zol87 via Flickr