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St. Augustine Old Jail History

group of guests and tour guide standing inside a cell at the Old Jail Museum in St. Augustine, FL


What well may be the only house of corrections that people actually want to visit, St. Augustine’s Old Jail is one of the few attractions of its kind and an absolute must for your vacation itinerary. This coral-colored prison masquerading as a hotel was a rather dire and harsh place for over 60 years. You’ll get to see the cells firsthand and learn of the many injustices that took place here, mainly from the crooked sheriff who oversaw the prison. Beware! They even say that the restless spirits of former inmates still roam the corridors yearning to be free!

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In 1878, Henry Flagler left the familiar confines of his tony and privileged life in New York City for a respite for his ailing wife. The oil magnate and industrialist traveled south to Jacksonville, Florida with his family on strict doctors orders so his wife could escape the intemperate winter of Manhattan and potentially recover from tuberculosis. Sadly, Mary Flagler would not survive long after they completed the journey. Shortly thereafter, Henry Flagler would remarry and make his way to the Ancient City, St. Augustine, Florida. Finding the area charming and brimming with possibilities but sorely lacking in accommodations, the businessman hit the ground running and began to make sizable real estate investments in the area which included the Hotel Ponce de Leon.

While he was busy conquering the state by connecting the bigger cities via his Florida East Coast Railway, he was also busy luring his rich northern colleagues to venture south to escape the bitter winters and to invest in the area.


In 1891, Henry Flagler offered to pay $10,000 to move the city’s prison from Cordova Street to a location just north of downtown on San Marco Avenue. He disliked the idea that such unsavory people would be housed near his beloved hotel and he didn’t want an eyesore that would strike fear in the hearts of the general public, to say nothing of his fat cat friends who might become discouraged from investing in the city. He also wanted the jail to blend in with the rest of the buildings in St. Augustine so, he decided to disguise it.

Built in the Romanesque Revival style and painted in an unassuming color that blended with the neighborhood, The Old Jail couldn’t have looked less than what it was. With the exception of the bars on the windows, which could have easily been interpreted as a style cue of the day, this house of corrections operated in near anonymity. His ruse worked so perfectly that visitors to town would often walk into the Old Jail asking for a room.


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The Old St. John’s County Jail in St. Augustine was so fascinating to go through. This jail could hold up to 72 prisoners and also housed the most violent and dangerous prisoners in their maximum security area, as well as having solitary confinement and a death row cell. Being an open air jail where the temperature outside is what the temperature inside is, prisoners were packed into cells sharing one bucket and the only way to get rid of the contents was to bang it against the window with thick metal bars. Even worse, the women’s cell had the window and the men’s cell didn’t so they would bang their bucket into their cell 💩😷 it was a working jail so the men worked sun up to sundown and the women cooked and cleaned up after the entire jail. Even WORSE, the prisoners were given the opportunity to bathe once a month. It was a single tub of soapy water outside that they all shared. One after the other they went in taking turns, all the men first and women last, at which this point it wasn’t soapy water anymore – it was more like a sludge 🤢 . . . #StAugustine #StAugustineFL #OldestCityInAmerica #History #Historic #HistoricBuilding #HistoricArchitecture #HistoricBuilding #HistoricJail #OldStJohnsCountyJail #Traveling #Exploring #FamilyTravels #InstaTravel #TravelGram #Tourism #Tourist #Instago #IgTravel #Visiting #RoadTrip #RoadTrippin #StAugustineLife #OldCity #OldestCity #FloridaStyle #FloridaLife

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Within the walls and behind the bars of this non-descript prison were some of the worst living conditions imaginable. This two and a half story building housed 72 male and 12 female inmates when at capacity. Half of those women were doomed to share a cell that had no electricity or running water until the prison closed in 1953. The sheriff, what one would consider a warden today, lived adjacent to the jail with his family and would enlist the female inmates to cook and clean after them and the rest of the male inmates. Many of the women here were brought in on trumped-up charges like being accused of low repute or of having a bad family name. Some of the men incarcerated here were also subject to the whims of the corrupt local authority.

All who were imprisoned here were obligated to perform hard labor in the fields or, if sufficiently infirm of health, in the jail’s front yard. The men were tasked with the harsh, outdoor work. There was even a lending program where the sheriff would line his dirty pockets with the money local farmers would give him in exchange for farm hands taken from the prison population. These prisoners were transported to and fro shackled in a caged carriage and would routinely return to the prison after their work was done with fresh wounds on their hands and shoeless feet. In these barbaric conditions, the average inmate survived two years before succumbing to disease, exhaustion or the hangman’s noose.


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Old Jail, built in 1890. #OldJail #StAugustine #Florida #History #ShotOniPhone

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For a part of the 60 years the jail was active, St. Augustine’s hardened criminals were overseen by the notorious Sheriff Joe Perry. Sheriff Perry was a calloused disciplinarian with a malicious streak that struck fear in even the toughest inmates of the prison who wasn’t shy about doling out punishment whenever his little black heart desired. Handy with a rope, Sheriff Joe presided over several executions on the grounds of this sinister “hotel” and it is alleged that the restless spirits of some of the prisoners who died here still can’t find peace and roam the halls of the prison protesting in agony. Some of the more well-known inmates to be condemned to the gallows were
Sim Jackson, who was hanged in 1908 after murdering his wife with a straight razor and Charlie Powell, who was accused of killing a man for spreading rumors about his wife.

There were eight recorded executions in the prison’s history. On the days when these executions took place, which were announced to the public ahead of time, the townspeople would flock to the prison grounds, even climbing telephone poles and walls to get a better look. Such a frenzy would ensue with these gruesome displays that the jail discontinued their practice of announcing the exact execution date, preferring to instead announce a more vague, window of time to discourage people from congregating in the streets in such high volumes.


After several changes of hands since the prison’s closing, Historic Tours of America, proprietors and managers of several well-known St. Augustine travel and tourism businesses such as Old Town Trolley Tours, Ghosts & Gravestones Tours, and Potter’s Wax Museum, purchased the Old Jail in 1999.

Listed in the National Registry of Historic Places, The Old Jail is a must-visit when in St. Augustine! Visitors will find that the Old Jail has been renovated to give tourists a glimpse into the daily lives of St. Augustine’s most notorious prisoners, as well as paint a portrait of what the penal system of the 19th and early 20th centuries looked like many years ago. Costumed actors tell tales of the jail and its occupants, and even book you as an inmate! Additionally, the Old Jail has a large collection of weapons for you to inspect up close along with one of the first ever fingerprinting kits ever issued in Florida that dates back to the turn of the 20th century. This was a revolutionary new tool at the time in law enforcement that increased the odds of capturing criminals instead of the innocent. The Old Jail is one of just a few prisons of its kind still standing and makes for a great sightseeing and historical adventure.

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