Honestly....
....I really just want to WoD by Night my city. Because Philadelphia is full of truly amazing and weird shit that you might not ever know about, even if you actually live here.
The Comcast Center is the tallest building in the city, run by an absolutely massive telecom giant that has extended its creepy monopoly tentacles into so many areas of the city. It claimed responsibility for lifting the Curse of Billy Penn. It has massive, massive video screens all throughout its lobby and hosts public events there, from concerts to sporting event-viewing, and so on. The screens are so large, they're a tourist attraction. People come into the building just to look at the giant TV-screens. You legit want to tell me the Technocracy DOESN'T run that shit?
Or South Street -- South Street that's home to Tattooed Mom's, and the Digital Ferret (basically the physical manifestation of Metropolis records), and was home to Zipperhead (punk shop of Dead Milkmen fame), and Harry's Occult shop (which was a creepy occult shop in the 'Leave It to Beaver' days, and that's just weird and amazing), and the super weird condom store that has a dick fountain, and the Wiccan store that's been there forever, and the home that Larry Fine of the Three Stooges was born in, and god knows how many skeevy tattoo shops, and head shops, and weird little bodegas. South Street is bounded by a neighborhood full of Federal-era houses that some of the richest people in the city live in, and South Street is a solid nine blocks of where they shoved all the 'freaks' into a self-contained neighborhood. It's like there's literally a barrier of containment around the place.
Or the Mutter Museum -- a museum of medical oddities founded in 1858, which was once the center of biomedical research in the city during the 19th century. The building is all Victorian gorgeousness, and yet houses the death cast of Chang and Eng, the original 'Siamese' twins, and the world's largest colon (it's super gross!), and Grover Cleveland's tumor, and jars full of organs, and wax models of syphilitic skin infections. I'm, like, 99% sure that the Ordo Dracul sleeps in the basement.
The Skulls fraternity they made that shitty movie about? It's a real thing. It was founded at UPenn in 1850. It's had wrongful death suits in recent years. What are they doing in there?!?
Eastern State Penitentiary -- the first true 'penitentiary' in history. It was abandoned by the city in 1971. It's been turned into a massive haunted house every Halloween since the 90s. It is supposedly truly haunted, and as someone who has worked there, I can verify that the place is eery and terrifying, even when you know it well. Ghost Hunters did an episode there.
The Mummers. They're Changelings. I just can't decide if they're Spring, or Summer, or both given their penchant for grand, ecstatic display -- and violent, drunken racism run amok.
The Pagans MC -- an outlaw, 1%-er motorcycle club located mostly in the mid-Atlantic. They generally fight with the Hell's Angels for territory, and their headquarters is in Delaware County -- just outside Philadelphia. They are so hyperviolent that they've run the Hell's Angels entirely out of town, and firebombed one of their bars.
You want to do gritty and ugly and violent and corrupt buried under a veneer of colonial beauty and respectability and history? You do Philadelphia. It's a weird, wonderful town.