Pittsburgh is a dump. You'd love it.
Things in Pittsburgh-
The Warhol Museum
The Carnegie Museum (great Dino display)
The Pittsburgh Zoo
A shit-ton of bridges
the incline
The old armory
Heinz Ketchup
some cool little breweries/sausage houses
A few cool dumpy coffee shops, vegan restaurants/venues, and art galleries
The Strip District- Ethnic food stores, street vendors, Primanti Brother's subs. It is a little dumpy place that is fun
The South Side- long strip of cool places, cool 50's diner with really great milkshakes here
Oakland- Hospitals and Colleges
Some good pizza shops
One of the US's largest Jewish communities- Squirrel Hill (cool town too)
Point State Park
To the north about 35 miles- McConnell's Mill and Moraine State Park (I'd suggest McConnell's Mill)
To the south- Laurel Caverns
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