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City-wise maybe Baltimore has (or had) the best chance for the weird type of vibe, but until the crime rate gets under control, I can't claim Baltimore as so much "weird" as say "violent." Even the nice areas are more "trendy" and "preppy" than say "hip."
For small towns, one might argue that Brattleboro, VT still has a little bit of that "keepin it weird" vibe going.
New orleans would top my list. I have heard the arts scene in the Garden District is pretty amazing and very bohemian. When I was there I saw more young black kids downtown drumming and listening to brass band music more than hip hop. I doubt any city in america has the history with music and food and interesting architecture, would be an amazing place to live.Savannah maybe as well, florida keys if you can afford it
Any city that advertises itself as weird... isn't.
Yeah, they are "faux-weird" who might be a tad weirder than normal and thus want to shine a spotlight on themselves as the ne plus ultra.
A friend of mine who's lived most of his live in New Orleans says "It would never even occur for NOLA to be anything but weird." Not east coast, but I think they win.
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