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Well, I am not originally form the US, but I have lived here for several years. And during those years Ive driven pretty much everywhere, both in the US and Canada, east of the Mississippi, from Miami to northern Quebec. And honestly, hitchhiking isnt as easy or as common over here, so keep that in mind. Now, with that in mind, some of the places which have relatively unique small towns with things to do and see are eastern PA, the Hudson Valley in NY, and Vermont.
If you want to be strict about only going to small towns, I would advise you against most of the states in the so-called deep south (GA, MS, AL, etc.) for 3 reasons: first, as population density is generally low outside of the big metro areas, small towns are relatively far from each other, making it a bit harder to see a lot of stuff in 5 days; the train and public transportation service is much worse than in the NE, which means you wouldnt really have an alternative to hitch hiking; and finally, most deep south states have not been as careful with historic preservation and the such as states up north.
The only exceptions to this would be the coastal towns, but then again they are not really "small towns." I am talking about Savannah, Charleston, etc.
But as I said, I only really know the areas east of the Mississippi.
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