I spent some time in Virginia in the 90s, and have spent a whole lot more time in Ohio/Kentucky in the past 6 years.
Virginia in the summer is absolutely beautiful (I was in Great Falls). Take a trip to Charlottesville - magnificent, and take a while to go around the University.
As for Ohio and Kentucky, some lovely little villages (you'd call them towns) like Mason, or Covington for example. In Kentucky, you have to get on the Bourbon Trail and visit a distillery or two. Wonderful history, lovely people. My opinion, of course!
I vaguely remember towns like Madison, Wisconsin, and Ann Arbor, Michigan from my 1974 choir tour - beautiful and quaint.
Goes without saying that I love NY and Chicago.
Never been further west than Minneapolis!