Pittsburgh is somewhere middle of the pack among the cities I’ve visited. Milwaukee is a much better city even though Pittsburgh (or Pennsylvania) may have a better political outlook.
East Liberty
This neighborhood is apparently being gentrified. Not very walkable. Lots and lots of roads with complex and dangerous intersections. Witnessed an accident on one of them while I was there. It’s very quiet… too quiet. A few blocks away, there was a more vibrant commercial street. Go a little further and you can get to Shadyside.
Shadyside
This place was neat. The commercial street had luxury retailers like Apple next to weird quirky local places like Tennis World. It didn’t make sense, but it was fun to walk around it. I got yelled at out of a car window here. Other people seemed nice for the most part. I got some decent bubble tea. Not quite the level of urbanity I’m looking for but very charming.
Strip District
The Strip District was an strip mall/flea market for cool people. The bike shop here is great and is probably where I would buy a bike if I lived here. The rest of it was neat to look at but there wasn’t much substance.
Downtown
Downtown is neat, but it’s a bit dirty and old feeling. It doesn’t feel vibrant like Chicago, Philly or even Milwaukee. I liked looking around, but I didn’t find anything that was actually interesting. The glass company buildings were neat to look at.