St. Augustine Old Jail
The Old Jail was completed in 1891, designed to look like a fine hotel on the outside (it has a wide front porch, and it's pink!), but a real frontier-era jail on the inside, one of the few surviving 19th-century places of incarceration. Built by Henry Flagler, the massive Queen Anne-style stucco building was located at a good distance from Flagler's own fine hotels, where he hosted many of the wealthiest people in the nation.
Costumed "deputies" show you around the cell blocks, the maximum-security area, and the surprisingly pleasant living quarters of Sheriff Joe Perry and his wife and daughters, who lived just across a narrow hallway from the inmates. Out back, the gallows stand in mute testimony to the rougher side of St. Augustine history. They serve to remind us of a harsher time, and go a long way towards explaining why The Old Jail is now listed as one of the most haunted sites on the National Register of Historic Places.