I'm in Pittsburgh. If you've never been here, the Incline is pretty neat to ride to the top of Mt. Washington. Great view of the city up there. Also might wanna check out the Carnegie Science Center and Andy Warhol Museum. If you're 21, the Hofbrauhaus is definitely a must visit.
As far as parks in the Pittsburgh area, the closest are probably McKinley and Imperial. McKinley is pretty grimey. Imperial is fun, some prefab stuff, but good tranny section. Hit me up when you get here if you wanna meet up and skate around town or whatever with some people.