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History and Facts About the Old Jail in St. Augustine

History and Facts About the Old Jail in St. Augustine

St. Augustine old jail

The Old Jail, a captivating historical attraction, invites visitors to step back in time and experience the daily lives of St. Augustine’s most notorious prisoners. The building, constructed in the Romanesque Revival style and painted in a muted hue, has been carefully preserved to maintain its authentic character.

Costumed guides, knowledgeable about the jail’s history and its former inmates, share thrilling tales of the lives lived within its walls. Visitors can even participate in the unique experience of being “booked” as an inmate, providing a firsthand glimpse into the challenges faced by those incarcerated in the past.

The jail’s extensive collection of weapons and artifacts offers a fascinating glimpse into the era. From antiquated firearms to prisoner-made objects, these items provide tangible evidence of the lives lived within the jail’s walls.

Old Jail Sheriff's office wall and weapons

As one of the few remaining prisons of its kind, the Old Jail is a must-visit destination for history enthusiasts seeking a unique and immersive experience.

Explore the History of the Old Jail

The Old Jail, a historic site in St. Augustine, Florida, served as a penal facility for over six decades, operating from 1891 to 1953. Its listing on the National Register of Historic Places recognizes its significance as a testament to the past and a valuable resource for understanding the region’s history.

The jail’s construction was initiated by Henry Flagler, a prominent industrialist known for his development of St. Augustine. Concerned about the safety and well-being of his guests at the opulent Ponce de Leon Hotel, Flagler sought to establish a secure facility that would maintain order in the city while ensuring the comfort and tranquility of his patrons.

Flagler’s initial concern was that the original jail’s proximity to his hotel might compromise the comfort and security of his guests. To address this, he ordered the jail to be relocated to a more distant location, further separating the city’s criminals from his friends and patrons.

The task of constructing the new jail fell to the P.J. Pauley Jail Company, renowned for their work on the infamous Alcatraz prison. Pauley’s team designed the jail in a Romanesque Revival style, carefully crafted to resemble a Victorian house. This architectural choice was intended to avoid alarming visitors to St. Augustine or creating an impression of high crime rates in the city. The only external indication of the building’s true purpose was the presence of barred windows.

Despite its outwardly benign appearance, the jail served as a formidable fortress, housing some of the most dangerous criminals of the era. The grounds of the jail also served as the site for capital punishment, where several individuals were executed on the gallows.

side view of the Old Jail in St. Augustine

The two-and-a-half-story jail had a capacity of 84 inmates, comprising 72 men and 12 women. While some of the female inmates were convicted criminals, others were imprisoned solely due to their questionable reputations. Women without strong family ties or husbands were particularly vulnerable to this practice, often finding themselves incarcerated despite having committed no crimes.

All inmates were required to perform labor as part of their sentence. Those who were physically unable to work in the fields were assigned alternative tasks, such as tending to the front garden. The jail’s reputation extended beyond its role as a correctional facility. It was also notorious for carrying out capital punishment. Eight men were executed on the gallows erected on the property during the jail’s operational period, a stark reminder of the severity of the crimes committed and the justice meted out within its walls.

Sheriff Joe Perry, a towering figure at 6’5″ and 300 pounds, ruled over the St. Augustine jail with an iron fist. Known for his strict enforcement of prison regulations, Perry took his duties very seriously. His imposing presence and stern demeanor instilled a sense of fear and respect among the inmates.

Even after his death, the spirit of Sheriff Perry is said to linger within the walls of the Old Jail. Many visitors have reported seeing his ghostly apparition, a chilling reminder of the jail’s past and the individuals who once guarded and incarcerated its inmates.

exterior shot of St. Augustine Old Jail and in the foreground is a statue of Sheriff Joe Perry sitting on a bench holding a shot gun with the words 'Sheriff Joe Perry, 1889 1897 / 1901 1919' painted on the bench

In 1954, a year after the jail closed its doors, it was transformed into a local attraction. Henry L. “Slim” McDaniel, a dedicated preservationist, undertook the restoration of the building in 1993. His efforts brought the Old Jail back to life, allowing visitors to explore the jail’s history and gain a deeper understanding of the lives of its former inmates.

Today, the Old Jail is owned by Historic Tours of America® and stands as a testament to the past. Visitors can tour the jail’s cells, explore the gallows and even experience the chilling sensation of being locked in solitary confinement. A visit to the Old Jail offers a unique opportunity to step back in time and learn about the history of the penal system in St. Augustine.

Facts About and Ghosts Stories of the Old Jail

Historical Artifacts

Original chains, handcuffs and prison uniforms are still present, offering a tangible connection to the jail’s past.

Guests can see Florida’s very first fingerprinting kit at the Old Jail.

Architectural Significance

An example of Romanesque Revival architecture, the jail is studied by architecture students and historians fascinated by its design and construction methods.

Violent Prisoners

Sim Jackson, a notorious prisoner at the Old Jail, was incarcerated for nearly decapitating his wife with a straight razor in 1906.

Another infamous inmate, Charlie Powell, was imprisoned for the murder of a man who dared to speak ill of his wife. Powell’s ghost is said to haunt the area near the gallows, seemingly reliving the harrowing events of his execution.

These two cases highlight the severity of the crimes committed by some of the Old Jail’s inmates. Jackson’s brutal act of violence and Powell’s murderous rage underscore the dark side of human nature and the consequences of unchecked anger.

Prisoner Escape Stories

Numerous tales of attempted escapes exist, though few succeeded due to the jail’s formidable construction and vigilant guards.

Poor Care

Meals provided to inmates were basic and often insufficient, leading to widespread malnutrition and related health issues.

A doctor only visited the jail during a hanging to pronounce the executed dead, so inmates often suffered through untreated illnesses and maladies.

Old Jail Fact

Sheriff Joe Perry's Office

The preserved sheriff’s office is part of the tour experience, giving visitors a glimpse into historical law enforcement practices.

Sheriff Perry's Presence

Some believe the spirit of Sheriff Joe Perry still roams the jail, maintaining a watchful eye on the premises.

Mysterious noises, cold spots and shadows in the dark near the sheriff’s office further these beliefs.

sheriff inside old jail

Haunting Voices

Visitors have reported hearing conversations and whispers in empty rooms, as if past inmates still linger.

There have also been reports of barks from guard dogs past echoing through the cell block.

The Ghost of an Inmate

A common sight is a man dressed in old prison garb, presumably a former inmate who never left.

Mysterious Footsteps

Many have claimed to hear footsteps following them as they walk through the jail, despite no one else being around.

Encounter With the Unseen

Tour participants report feeling watched or lightly touched by unseen hands, adding to the eerie atmosphere.

Reportedly, there is an entity known as “The Crawler” who moves along the cell floors and follows visitors around the cell block.

Ghost Tour Witnesses

Ghost tours attract those curious about the paranormal, with many attendees sharing similar stories of spectral encounters and odd occurrences.

The solitary cell is a particularly daunting challenge for visitors. Those who dare to enter must sit alone in the far left corner. Many claim to have witnessed a shadowy figure lurking in the darkness, a specter that seems to scurry toward them and attempt to tear at their clothes.

FAQs

Visitors on a tour of the Old Jail can expect an immersive experience that blends history with the paranormal. The tours are guided by knowledgeable hosts who share detailed accounts of the jail’s construction, its notorious inmates and the conditions they endured. Additionally, the tours often highlight the eerie aspects of the jail, recounting ghost stories and paranormal encounters that have been reported over the years. Participants have the opportunity to explore various parts of the jail, including the cells, the gallows and even the preserved sheriff’s office, making for an engaging and informative visit.

A typical tour of the Old Jail lasts about 45 minutes to an hour. This duration provides ample time for visitors to learn about the history of the Old Jail in St. Augustine, hear the chilling tales of ghostly apparitions and explore the different sections of the jail. Some specialized ghost tours may differ in length, offering more in-depth explorations of the paranormal aspects.

The Old Jail is architecturally unique due to its Romanesque Revival style. This architectural approach is characterized by its robust and grandiose design, featuring rounded arches, heavy stone construction, and intricate detailing. Historians and architecture enthusiasts find the Old Jail particularly fascinating due to its durable construction methods, which have contributed to its longevity and historical significance. The building stands as a remarkable example of 19th-century penal architecture.

Yes, the Old Jail is family-friendly. While the jail has a reputation for its ghost stories and eerie atmosphere, the tours are designed to be both educational and entertaining for visitors of all ages. Guides tailor their stories and presentations to suit a general audience, ensuring that children and adults alike can appreciate the historical and paranormal aspects of the jail. However, parents should use their discretion based on their children’s sensitivity to spooky tales before booking one of the paranormal-focused tours.

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