Friday, September 22, 2023

The Haunted History at the Old Jail in St. Augustine

*Originally published June 13, 2021 as a promotional piece. Some information may be missing.

 In 1878, oil magnate and industrialist Henry Flagler left New York with his ailing wife and headed to Jacksonville. On doctor's orders, they were advised to leave the climate of Manhattan for warmer, milder Florida so that Mary Flagler could try to recover from tuberculosis. Sadly, she didn't survive the trip. Shortly after her death, he remarried and moved about 35 miles further south to St. Augustine. He found the area beautiful and full of possibilities for tourism, but severely lacking in accommodations. He began making large real estate investments, including his flagship hotel, the Hotel Ponce de Leon (now Flagler College).

The city jail at that time was not only an eyesore, but it was within view from one of Flagler's hotels. He knew that his rich guests wouldn't want to see the jail while they were vacationing, and that its presence outside their hotel room windows could diminish their experience in such a charming city. Furthermore, he feared that such an unpleasant looking building would discourage his high profile friends from investing in St. Augustine. So, in 1891, Flagler contracted with the company that would eventually build Alcatraz to construct what is now known as the "Old Jail." It was built just north of downtown on San Marco Avenue, and disguised so as not to appear to be a jail from its outward appearance.

Listed in the National Registry of Historic Places, the jail was built to look like a hotel in the Romanesque Revival Style. It was painted an unassuming color. The walls were over 20 feet tall and so thick that no sound could transcend the cells and be heard by outside ears. Aside from the bars on the windows, no one passing by would ever have known it was a jail.


The conditions inside and what transpired within this beautiful Victorian building, however, earned the Old Jail its reputation as one of the most haunted spots in the city.

The jail not only housed both male and female inmates, it was also the home of the sheriff and his family. It was the city's only jail for more than 60 years, remaining open and operational until 1953.

While the sheriff's quarters were quite comfortable and well appointed with all the necessary comforts of the day for him and his family, the inmates' cells were a far cry from that. By today's standards, they would be considered unlivable for humans.


The windows didn't have any glass or protection from the outdoor elements - just the bars needed to prevent the prisoners from escaping.

The concrete and metal of the cells made for a very cold, very stern environment.

No blankets or pillows were provided. The mattresses were stuffed with Spanish Moss, so they were often infested with bugs. There were no bathing facilities or sanitation for human waste, so the inmates couldn't bathe and there was a constant stench that could not be eliminated.

The maximum security cells were located at the back of the building, equipped with stockades, a torture cell, and a clear view of the execution area. The solitary confinement cell didn't even have a bed.


There was much sickness and death in the Old Jail, far beyond the executions that took place there. There were eight reported hangings on the site, as well as many other unnatural deaths.

In truth, the inmates who were incarcerated there were the worst of the worst. Many did not survive their sentences. Although they were horrific people who had committed horrific crimes, the treatment they received at the hands of their jailers was often less than humane, including beatings, tortures, and starvation.

Paranormal researchers believe that these events caused the spirits of some of the inmates to linger within the Old Jail, resulting in the many mysterious and inexplicable events that happen today.

Some reported paranormal experiences include:


~ People who live near the jail as well as tour guests report hearing the sounds of footsteps walking around inside.

~ Visitors and workers have reported the aroma of sewage in the air although there is none to be found.

~ Although there are no longer any dogs living at the Old Jail, there are reports of dogs barking.

~ Tour guests have reported hearing voices in the cells and hallways, as well as the sounds of wailing and moaning coming from the maximum security and solitary confinement areas.

~ Some visitors have reported hearing the voice of a little girl coming from the sheriff's quarters.

~ There have been accounts of people people feeling like a cold hand is touching their shoulder, as well as the sensation that someone is pulling at their hair or blowing on them as they walk by.


Today, the Old Jail has been renovated to give tourists a glimpse into the daily lives of St. Augustine's most notorious prisoners and what it was like for them living under the penal system of the late 19th and early 20th centuries.

Costumed actors tell the stories of the jail and its inmates as you tour the space and examine the collection of weapons and artifacts. It is one of the few prisons of its kind still standing today. "The Old Jail After Dark" is a 45 minute experience that allows visitors to participate in an actual paranormal investigation at the Old Jail. Tickets are available at Old Town Trolley Tours.

If one of your reasons for visiting St. Augustine is the paranormal experience, like it is for us, this place needs to be on your list of tourist stops, and I would even recommend taking not only the daytime tour, but the "after dark" tour as well to get the full experience.



167 San Marco Ave.
St. Augustine, FL  32084

904-829-3800

Do you have any information or personal experiences to share about this entry? Let us know in the comments, and your contribution could be included in a future update to this entry!

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