[pukka_my]

How small is small? Portland is nice, as is Austin. Boulder and Madison are both nice but full of hippies. Boston, Pittsburgh and Philly are all pretty cool if you are thinking mid-Atlantic/northeast; Charleston and Savannah are great if you want to be further south.

[MatthewPhillips]

Well Philly is the #5 biggest city in the U.S., so I'm guessing it's out.

I'd say you have to be less than ~350k to be considered a small city.