We went from Gettysburg, Pennsylvania to Cleveland, Ohio to Chicago Illinois. I got to drive a good chunk of it too. I loved driving in the rural areas, so comforting. We stopped by the 9/11 memorials in Pennsylvania, the Tower of Voices.
Chicago was something, lots of people and a change of scenery compared to PA. We went to fancy dinner places and we suffered the exchange of wearing my heels since I didn't know we had to walk back from the restaurant to the hotel. So we each walked a half mile in my heels, literally.
We then went to Wisconsin where I fell in love with the place. Then off to Mackinaw Island, MI. Cute place! And then we drove 15 hours straight to get back to CT by 0100. One hell of a road trip there.