Photos by Kelsey Walters

Like any city or town with a long history behind it, St. Augustine is no stranger to scary ghost stories and unusual happenings. Seeing as it lays claim to the title of the oldest established city in the United States, it’s no surprise that there’s plenty of chronicles of sordid ongoings throughout the city’s cobblestone streets. 

In fact, on any given night, as soon as the sun goes down, you’ll likely spot a number of ghost tours haunting the streets. St. Augustine’s “nightlife” is more focused on the dead, with haunted trolley and walking tours being their bread and butter.

Old Jail After Dark – St. Augustine 

A new tour, however, hopes to stand out in the creepy crowd with a different offering…that’s not exactly a tour at all. The Old Jail, located within the Old Town complex just outside of the main downtown stretch, has quite the unsavory history. In operation from 1891 to 1953, it was home to St. Augustine’s most violent criminals, under the iron fist of Sheriff Joe Perry for much of that time. Built by the same company responsible for the infamous Alcatraz prison, it was meant to house around 72 prisoners at a time. Instead, it was stuffed to the brim with thousands of bodies – sometimes as many as 12 men in a four-man bunk – leaving prisoners to literally fight for their lives. The gallows out back carried out capital punishment, while others were set out in a massive cage hanging from the trees towards the street, setting an example for passersby. 

With thousands of deaths, and even more thousands experiencing endless pain and suffering, it’s no wonder why this jail claims to be one of the most haunted spots in town. The Old Jail After Dark tour takes you inside the haunted halls, not just for a history lesson, but to hunt for a haunting yourself with a DIY paranormal investigation. 

Born out of COVID protocol, the small tour is kept to a maximum of 10 participants, although the building is rather large. This also helps with your investigation, as there’s plenty of room to space out without interference. Out front you’ll get the lowdown on some of the more sinister history of the building, like the innocent men sent to their deaths at the hands of Perry. 

Inside, you’ll be equipped with all the tools you need to seek out a spirit, including dowsing rods, electromagnetic field detectors and FLIR handheld thermal cameras – if you dare. Our group split up over the two main floors and we set out for some paranormal activity. You’ll have 45 minutes inside for your investigation, but it goes by quickly especially if you’re experiencing a lot of activity. Given the nature of this tour, it is not suitable for young children and only available for ages 13 and up. 

Ghost Hunting Experience in Florida

Scott and I went upstairs and straight to Perry’s bedroom (yes, he lived right there in the jail, along with his children…what a creep). Seeing as this was mostly a men’s prison, with only a small holding area for women who were swiftly arrested and plucked from the streets for “kitchen work,” Perry seemed to have it out for punishing men, and Scott was no exception. As soon as we crossed the threshold into the room, he felt a sensation of a hand on his neck and later his chest. A feeling of invisible cobwebs crept across his skin as we tried to communicate with a dual sweep frequency ITC research device, otherwise known in the ghost hunting trade as a Spirit Box. 

While you hold a normal conversation, the Spirit Box sweeps radio frequencies creating a white noise effect that is said to allow a spirit’s voice to break through and communicate. While it is easy to dismiss this phenomenon as janky technology or coincidence, I will say that the only time we experienced any sort of activity with the Spirit Box were the two times we stepped into Perry’s room and were able to carry on a back-and-forth conversation. 

We also took a shot at sitting in Perry’s original desk chair, which has been known to irritate him. When I took a seat, nothing much happened. When Scott sat down though, the thermal camera jumped wildly back and forth by 10 to 15 degrees, even though no one was moving and the air conditioning hadn’t kicked on yet. 

Others in our group stuck to one spot and waited for activity to come to them. Another subsect ventured into the women’s cells and solitary confinement, where they claim they were pushed and scratched. While I’m not entirely set on what I believe when it comes to the paranormal, I think (like most activities) if you allow yourself to believe, even just for the night, and lean into it, you’re going to have a lot more fun than the sceptics. If you’re dead set on having a life changing experience, or conversely on believing nothing will happen or it’s all just chance, you may be disappointed and you’re better off just going with the flow and enjoying the unique experience. 

No matter what you believe, I can guarantee that you will get spooked on your tour in the dark, thanks to the incredibly lifelike mannequins placed throughout the jail. You’ll round corners to jump back and find them hiding in corners or hands reaching out from cell doors, while others appear to be dead asleep (hopefully?) in bunks. 

When our time was up and everyone headed to the central kitchen command post to share their experiences, I held back for a moment to grab one last photo of Perry’s figure looming over the general population cell block. While I did so, I couldn’t shake the ominous feeling that I was being watched or followed. As I headed down the stairs, I caught a glimpse of something, or someone, out of the corner of my eye and felt something brush my leg. It still gives me the creeps just looking at this photo. 

While I didn’t come away from this experience with indisputable evidence of the paranormal, I did get another spooky experience to tuck in my belt, and it certainly got me in the mood for Halloween! 

OLD JAIL AFTER DARK 

167 San Marco Avenue, St. Augustine 32084 

TrolleyTours.com/St-Augustine/Jail-After-Dark-Tickets 

(904) 701-0083 

FB: @OldTownTrolleyStAugustine 

Insta: @OldTownTrolley 

Thu – Sun: 8 – 11 p.m. (must reserve in advance) 

$31.94/person