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The Old Jail, St. Augustine, After Dark

From housing some of the county’s most notorious prisoners to becoming a hot tourist spot, the Old Jail has become a fascinating part of St. Augustine’s history.

The Old Jail, formerly St. John's County Jail, is a historic jail in St. Augustine, Florida, nestled in the Old Town Trolley depot and within walking distance of the Ripley's Believe Or Not Odditorium.

Devil In The Details: The History of St. Augustine’s Old Jail

The history of the Old Jail starts off rather simply. It was built in 1891 and served as the county jail for 62 years.

But let's take a step back. The history of St. John's County Jail starts with a millionaire. Industrialist and tourism tycoon Henry Flagler had just left New York City for Jacksonville, Florida, with his ailing wife. He'd been advised to escape the brutal weather of Manhattan for a more temperate climate so his wife could potentially recover from a bout of consumption. Unfortunately, she would not survive.

Henry Flagler soon remarried and settled in the Ancient City of St. Augustine, Florida. Being the mover and shaker he was, he saw the small town's potential as a prominent tourist spot. But the area was severely lacking in accommodation. He then set off in search of some prime real estate on which to build an extravagant hotel, the Ponce de Leon.

He set his sights on a piece of land that overlooked the county jail. Now, in 1890, the St. John County jail was a true eyesore. To get the seedy claptrap of a building out of his sights, Henry donated $10,000 to the St. John County Commissioners - this was quite the cushy deal in 1890.

As a result, the jail facilities were moved to a new location several blocks from their original site. With a rich building fund, they hired The Pauly Company to design the new jail. It's important to note that this was the same professional outfit that would go on to build the infamous Alcatraz Prison.

With some input from the wealthy donor, the new St. John's County Jail was designed to look friendly on the outside so as not to deter the drove of tourists that would visit St. Augustine during the winter months.

But, this was merely a disguise, for, within its walls, the Old Jail housed St. Augustine's most dangerous criminals and was a madhouse characterized by cruelty and depravity.

Gallows with a noose at the Old Jail attraction in Saint Augustine Florida

Uncovering The Dark Side St. Augustine’s Old Jail

Like many jails of old, the conditions at St. John’s County Jail were nothing short of deplorable and inhumane. At its peak, the story building held a total of 84 prisoners, 12 of whom were female. Every inmate was required to labor off their sentence, be it in the fields or front garden. There was no electricity or running water.

Baths were infrequent, and toilet facilities were almost non-existent as they consisted of only one bucket per cell. Considering some cells housed up to 6 inmates, it’s not surprising to hear that violence, death, and disease ravaged the prison.

The Old Jail also had a Death Row cell for those condemned to die. A total of eight men were hung from the gallows throughout its history. It's quite unfortunate that the prison authorities didn't quite understand the science of hanging someone to death. The length of rope and weight of the person have to be carefully considered to provide a humane execution. Those executed at the Old Jail suffered a torturous death, some of them taking 14 minutes to die.

But were the prison officials really unaware of the science? See, the philosophy of the jail was that prisoners were there to be punished, not rehabilitated. The jail conditions and tales of medical experiments and abusive guards support this philosophy.

Prisons have long been some of the most dangerous places on earth, and the Old Jail was no exception. Dysentery and communicable diseases killed their fair share of inmates. Others died from abuse and accidents and at the hands of other more violent prisoners.

There's trauma within the walls of the Old Jail. A trauma so eerie you can almost experience it yourself. Grim, violent deaths have a tendency to tether the souls of the dead to the realm of the living. There have always been rumors of ghosts on the property - immortal souls doomed to relive the miserable lives over and over.

Visiting the Jail Turned Museum

There’s a grim yet almost whimsical elegance to places whose walls are steeped in their tragic past. Whether you're looking to catch a glimpse of a spirit wandering or feel a chill in a dark room, the Old Jail has plenty of haunting, creepy experiences to offer.

The creek of a floorboard or grim tales told by costumed actors is just the beginning. The question now is: Do you dare explore?

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