This massive Gothic-styled fortress, now mostly in ruins, was built almost 200 years ago in 1829. With encircling walls as high as 30 feet, the pen represents a rejected institutional idea—that through isolation and complete silence criminals would become penitent and feel true regret. Take the self-guided audio tour narrated by actor Steve Buscemi and learn about the prison, once the most famous in the world that housed Al Capone and “Slick Willie” Sutton. Closed in 1971, today it remains only partially renovated with many crumbling cell blocks still on view. If you think you can handle it, check out the venue's annual “Terror Behind the Walls” Halloween haunted-house event each fall.