I don't know if I'm alone in this, but I used to love going to small towns and visiting the bars. You meet the coolest people over a pool table. Aside from tourist attractions (most of which is rarely better in real life than in a picture) big cities all offer the same stuff to do. You can't have any great experiences with people you meet either because people in big cities don't talk to strangers.
So, it was always off to the small towns and shit-hole bars for me. You meet the best people and sometimes that leads you on some grand adventures. For instance, I ended up going to a small town called Joyce, Washington. I hit the bar there and met a group of friends when my turn came up on their pool table. That led me on a three day adventure that involved old ww2 bunkers, a natural hot spring, a rain forest, tide pools, tons of alchohol, and the amazing company of an extremely friendly girl who's name now escapes me (sarah? cindy? serena? oh hell).
You can never have that experience in a large city. That's just one of many fond memories that I have of small town bar hopping. I wouldn't trade them for all the tourist attractions in the world. Just one word of warning, not all small towns are welcoming. Sometimes you end up hitting on the wrong girl and Joe-billy-bob doesn't like it. I would only give two pieces of advice though. Prior to drinking in a new town, always get a hotel room in advance and always program the local taxi's number in your phone, even if you don't use either of them.