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Oddly, it seems like Michigan south to north would be kind of interesting. You'd need a place with enough small towns to get from place to place, and I think it would work. You could also walk along Lake Michigan or Superior a good stretch of the way, and the Upper Pensinsula would be a nice reward at the end.
Florida, North Carolina, and Massachusetts could also be interesting (N-S for FL and W-E for the others).
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