When I travel through the neighborhoods in Pittsburgh, the one thing that consistently surprises me is how many different cities it reminds me of as I roll through. You can tell that the city has lived through a number of eras simply because of how different the neighborhoods appear in terms of building trends, size, material and density. Certain areas constantly remind me of home and certain areas remind me of cities I've only traveled through and felt a sudden connection to.
For instance, the South Side is an area that I consistently feel comfortable in because it's the closest thing I'll probably get in the midwest to walking the crowded, orange-cone laden streets of Philly's South Street. Save New York City or places in the biggest cities in America, South Street is one of the densest shopping districts. It's an experience all by itself. But, South Street is gritty, it's urban and in many spots, harrowing to non-city-dwellers.
South Side is one of those as well – tall buildings, brick construction, large windows and a city street packed with quirky, hipster shops and incredible restaurants –– and not to mention a couple of bums! Check out the comparison.
Bottom is South Side and top is South Street:


Seems pretty similar, no?
Additionally, places like Oakland remind me so much of Center City, Philadelphia - spaced out, urbanized and weathered! It's great! Even someone as particular about cities as me, there's always something in Pittsburgh if you're willing to peer around for it. Let that be a lesson to you other Philly transplants: it's out there in Pitt, but chances are, it's hidden deep underground.