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.
St. Augustine's Old Jail
167 San Marco Ave., St. Augustine, FL 32084