I Want to Go On a Road Trip

This has been my new hobby. Just taking weekend trips with my friends. We only go once a month though. Mainly staying in the north east but also been going up in to Canada quite a bit. The last city was Pittsburg which was a blast. We will going back for sure we already decided. Next city though Cleveland. We take mostly country roads which is the coolest thing to me. Just looking for cool small cities or even little towns that are all about having a great time. So if you have any ideas up here in the north east let us know :). Things we like to see: Bridges (Yea I know it weird but I love them!!) We love good restaurants but not touristy ones, if there is a cool water front or an awesome down town strip is always cool!