Crown Point, Indiana
Of all the former prisons on this list, the Old Sheriff's House and Jail probably retains the most prison-like atmosphere of any of them. That's on purpose, since the site is now owned by a historic-preservation foundation. Parts of the building can be rented out for private parties, and volunteers also give historic and paranormal jailhouse tours and run a haunted house every October.
The main jail building dates back to 1908, when Lake County built a new, larger jail in Crown Point to replace its old one. Indeed, the jail was considered one of the best in Indiana at the time, and reputed to be escape-proof — until March 3, 1934, when the notorious bank robber John Dillinger escaped from the Crown Point jail and fled to Chicago, where FBI agents shot and killed him outside of Chicago's Biograph Theater a few months later. In 1988, local history buffs formed the Old Sheriff's House Foundation. The following year the building was added to the National Register of Historic Places, and in 1990 the foundation acquired the old building and started the process of restoring it to its former glory.
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