Eastern State Penitentiary Philadelphia
Spooky!
Admittedly the best time to see this place is near Halloween as they do a fantastic job of scaring the bejeezus out of you! The waiting in line can be rough but its totally worth it. If you however don't need the daylights scared out of you, you can always go during the day for the creepy tour.
Eastern State Penitentiary is the first prison to use the term "penitentiary" as it was a place for you to find penitence. The rooms had only sky lights in them so the only person you would commune with was God, or that's what the concept was. However if you know anything about being alone in a room with or without God it can eventually drive you insane which is what took place here.
Home to some of the most notorious gangsters of its time, most notably Al Capone who lived like a king while there. However many of the other prisoners were, what we would consider today, tortured and if they didn't have issues when they arrived they most likely developed them inside the amazing walls of this place. Again though, Halloween is they way to really see this place, it is creepy!
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