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I would get the Wisconsin and Illinois Bicycle maps, you can pretty much connect the dots on trails that run between the two cities. I couldn't give you a list of all the roads and trails I take, it seems every time I make the trip I do it in a slightly different way. There are some important things to remember, Avoid Racine by keeping on 31, you have to jog a little and get on Y. Its a bit nerve racking for a moment but is much better than traversing Racine. Going through Racine always seems to find me lost, and every time I'm confident that I remember the right way. Save yourself the trouble and just use the highway. Kenosha can bit a little tricky too, Stay on Y catch the MLK Trail for a short stint, then take G till the trail picks up again. Those are my suggestions for the most confusing part of the trip. See you out there, I hope to be making this trip every couple weeks or so.
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