Road trip NY => Kentucky => Chicago....where to eat??

Hi All,
I'm new to this site but love it straight away.

I'm planning on flying into NY around halloween and doing a road trip to Chicago via Kentucky.

It'll probably be 3 days in NY and 10days on the road.

Obviously food could dictate some of the route. Can you guys recommend the places i should visit and where to eat and the places that i shouldn't miss?

cheers
Frizz

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