The Old Jail, St. Augustine: A Prison Shrouded in Mystery and Ghostly Encounters

  • By: Timothy Rose
  • Date: 21 December 2023
  • Time to read: 6 min.


A tour through the picturesque town of St. Augustine, Florida, may lead you to an unusual tourist spot: The Old Jail. Known for its chilling history and reports of ghostly encounters, this imposing relic of St. Augustine’s past serves as one of the city’s most haunted locations.

History of The Old Jail

The Old Jail
The Old Jail – Credit Jared

Constructed under the direction of Henry Flagler in 1891, the Old Jail of St. Augustine, often referred to as the Authentic Old Jail, is an intriguing part of the city’s rich historical tapestry. Flagler, a well-known industrialist, real estate magnate, and founder of the Florida East Coast Railway, commissioned the new jail’s construction to remove the unsightly original jail from the view of his affluent guests at the Ponce de Leon Hotel.

The new jail, positioned remotely from the city center, was built by the Pauly Jail Building Company of St. Louis, Missouri, renowned jail builders of the era. Unusually, the Old Jail was designed in a Romanesque Revival style, causing it to resemble a Victorian home more than a traditional prison.

The structure was unique in that it doubled as the sheriff’s living quarters, housing the city’s most hardened criminals while also providing a home for the sheriff and his family. This unique feature adds another layer of intrigue to the Old Jail, distinguishing it from other structures of its time.

Haunting Legends and Supernatural Phenomena

The Old Jail in St. Augustine, Florida, holds a captivating paranormal history that continues to intrigue visitors from all over the world. Constructed in 1891, this historic building served as the county jail for over six decades and witnessed the confinement of numerous criminals, some of whom were infamous figures. However, as the jail closed its doors, a new chapter of eerie tales began to emerge.

The Old Jail – Credit Allen Forrest

Sheriff Joe Perry

Guests and staff alike have reported spine-chilling encounters, with apparitions of former inmates, like the notorious Sheriff Joe Perry and his gang, roaming the dimly lit corridors.

Sheriff Joe Perry was a notorious figure in the late 19th century, known for his criminal activities in and around St. Augustine, Florida. He was the sheriff of St. Johns County and became involved in various illegal enterprises, including bootlegging and gambling. Sheriff Perry and his gang were infamous for their ruthless methods and control over the local criminal underworld.

Read Also: Missouri State Penitentiary

During his time as sheriff, Joe Perry ran a corrupt operation, protecting criminal activities and intimidating those who dared to challenge him. It is said that he ran a secret underground network that allowed him to transport illegal goods and contraband without getting caught by law enforcement.

Sheriff Joe Perry’s reign of terror eventually came to an end when he was caught and arrested in 1914. He was convicted of multiple crimes, including murder, and sentenced to life in prison. He was sent to serve his sentence at The Old Jail in St. Augustine, where he remained until his death in 1927.

Henry Flagler

Additionally, the spirit of a female inmate, whose crime remains unknown, is said to wander the cells, adding to the haunting ambiance. As if the past clings to the building, the ghostly presence of influential historical figures like Henry Flagler, the prominent developer of Florida’s east coast railroad, is also rumored to linger within the jail’s walls. Some believe that former wardens and guards may still oversee the premises in the afterlife. Moreover, the lingering spectres of the hangman and countless other inmates, each with their own tragic stories, contribute to the eerie atmosphere and paranormal activity reported in the building.

Even present-day tour guides and staff have experienced unexplainable occurrences, further fueling the belief that The Old Jail remains a hotbed of ghostly manifestations. Today, as a preserved museum, guided tours offer brave souls the chance to explore the haunted history of The Old Jail, bringing the past to life with chilling encounters and spine-tingling stories of its rumored ghostly inhabitants.

Popular Culture and Media Coverage

The Old Jail in St. Augustine, Florida, has left a lasting impact on pop culture and media, featuring prominently in various books and movies, as well as becoming a subject of fascination for paranormal enthusiasts.

As a historic landmark with Victorian-style architecture dating back to 1891, the Old Jail‘s dark past and eerie ambiance have captured the attention of filmmakers and authors alike. In the horror film “Gore Orphanage” (2015), the Old Jail served as a haunting backdrop, adding to the movie’s eerie atmosphere and contributing to its chilling narrative.

Moreover, the Old Jail‘s reputation as a haunted hotspot has drawn the interest of paranormal reality TV shows, like “Ghost Hunters,” which dedicated an episode to investigate its alleged ghostly phenomena. This exposure in popular media has further solidified its status as a site of supernatural interest.

In the literary world, the Old Jail‘s spooky tales have found their way into books like “Ghosts of St. Augustine” by Dave Lapham, where the haunted history of the city is explored, likely featuring accounts of the Old Jail‘s chilling legends.

Investigation and Research Efforts

Paranormal investigators, drawn to the tales of apparitions and unexplained phenomena, have extensively studied the Old Jail. Results often include unexplainable electronic voice phenomena (EVPs) and sudden temperature drops, pointing towards potential paranormal activity. However, skeptics suggest that this might be due to the building’s old age and unique acoustics.

Visitor Experiences and Urban Legends

Tales of spectral figures, strange sounds, and unexplainable experiences have become a common thread among visitors’ stories. These eerie encounters, coupled with the grim history of the Old Jail, have given birth to several urban legends, further cementing its status as a hotspot for paranormal activity.

The Old Jail – Credits grimmlifecollective

Preservation and Tourism

Recognizing its historical and cultural significance, efforts have been made to preserve the Old Jail. It now functions as a museum, offering guided tours that bring to life the building’s past and its chilling ghost stories. This unique blend of history and mystery significantly contributes to St. Augustine’s tourism industry.


The Old Jail stands as a chilling reminder of St. Augustine’s past. Its walls, steeped in history and shrouded in mystery, invite both the curious and the brave to explore its ghostly secrets. The Old Jail exemplifies that history, paired with a dash of the supernatural, has an enduring allure, captivating generations of visitors.

Frequently Asked Questions (FAQs) about The Old Jail, St. Augustine

Q1: Where is The Old Jail located?
The Old Jail is located in St. Augustine, Florida.

Q2: Can I visit the former jail? Yes, the former jail is now a museum that offers guided tours to visitors.

Q3: What kind of paranormal activities have been reported at this place? Guests and staff have reported various supernatural phenomena, including apparitions of former inmates, disembodied voices, and unexplained movements or cold spots.

Q4: Has this location been featured in any media? Yes, this place has been featured in various books, documentaries, and paranormal-themed TV shows due to its reputation for ghostly encounters.

Q5: Have any famous inmates been incarcerated here? This place housed a variety of criminals during its operation. The most notorious of them were the famous sheriff Joe Perry and his crew.

Q6: Are there skeptics about the hauntings at this location? Yes, while many believe in the hauntings at this location, skeptics argue that the supernatural phenomena reported could be explained by the building’s old age and unique acoustics.

Q7: How is this location preserved today? This location is preserved as a museum, offering guided tours to visitors that cover its rich history and rumored ghostly encounters.

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