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Nashville to Chicago

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Hello, All

My husband and I are planning a road trip from Nashville, TN to Chicago, IL in late October. We would love some advice on what to do "off the beaten path" in the following places:

Nashville, TN
Lexington, KY
Madison, IN
Chicago, IL

We are big fans of getting out of the touristy spots and getting into the local vibe. We love hotels and restaurants that give us the true experience of where we are staying. Don't get me wrong, you will definitely find us at the honky tonks on Broadway, etc., we just would like advice on the not so well known spots as well.

Thanks, All!

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