Old St. Johns County Jail — St. Augustine, FL

Where Pastel Walls Can’t Hide the Dark

There’s a strange kind of beauty standing on San Marco Avenue — a two-story Romanesque Revival building shaded by palms and painted the softest bubblegum pink. From a distance, you could mistake it for an Old Florida inn, the kind of place with rocking chairs and lemonade on the porch.

But that’s the trick.
This is the Old Jail — and nothing about its history is sweet.

A Prison Disguised as a Resort

Step back to 1891. Industrialist Henry Flagler was building his luxurious Ponce de León Hotel just down the street and needed a way to keep the “less appealing” side of town from scaring off wealthy guests.

So he paid to build a new jail — one that looked like a resort, but functioned like a fortress.
Thick coquina walls. Pretty arches. Bars hidden in plain sight.

A good façade keeps questions away.

Inside, reality was brutal.
The cells had no glass windows, just open slats — letting in suffocating heat, biting insects, and the kind of Southern humidity that clings to you like guilt. Prisoners slept on Spanish moss mattresses… usually with fleas already in residence.

It could hold 72 men and 12 women. Some were hardened criminals. Others were simply women jailed for having a “questionable reputation.” Translation: society was harder on the wrong people.

And overseeing it all?

Sheriff Joe Perry — The Man They Still Hear

Sheriff Joseph R. Perry ran the Old Jail from its opening in 1891 until 1919.
Six feet five. Three hundred pounds.
A walking warning sign.

Stories paint him as strict at best and cruel at worst. Prisoners feared him — and some say they still do. Staff and visitors have reported hearing heavy footsteps pacing the upstairs hall… long after closing time.

And then, of course — the gallows.
Eight executions happened here. Eight lives ended on this patch of ground, the energy of their final breaths sinking into the dirt and never quite leaving.

The building is on the National Register of Historic Places today.
Not because it’s pretty — but because the past can’t be forgotten.

When the Sun Goes Down…

The Old Jail is eerie enough in daylight, but nighttime is when the walls start whispering.

Visitors report:

• Footsteps in empty hallways
• Chains clanking against nothing
• Soft crying from the women’s cells
• Sudden cold spots
• The feeling of being watched

Some say they’ve felt an icy hand brush their shoulder.
Others swear something tugged their hair.

The solitary confinement cell — a cramped box of concrete, iron, and regret — is considered the most active. Guests are challenged to sit alone in the dark corner and wait.

Most don’t last.
Some say a shadow starts moving before your eyes adjust.

The two most talked-about spirits are Charlie Powell, executed near the gallows, and Sim Jackson, imprisoned for murdering his wife in 1906 — his presence reportedly heavy and angry.

Even the dogs bark at empty corners.
Even the brave don’t linger.

I know because my son and I toured the Old Jail with Ghosts & Gravestones.
Let’s just say the darkness there feels… occupied.

Echo’s Corner

Did You Know?
The Old Jail was built by the same company that constructed Alcatraz.
No wonder so many souls here never made it out — in this life or the next.

Whispers Say…
Some guides claim they’ve heard low growls in the women’s wing — even though no animals live here. Whether it’s a phantom guard dog or something older… the walls won’t say.

If You Visit

📍 Location: 167 San Marco Ave., St. Augustine, FL
Tour Style: Daytime history, nighttime ghost tours
Time Needed: 45–90 minutes
Kid-Friendly: Yep — but nighttime tours can get intense
Best Experience: After dark… if you dare

Pro Tips:

• Book nighttime tours early — they fill up fast
• Wear bug spray (ironically, still a thing)
• If you’re claustrophobic, skip solitary
• Keep your camera ready — shadows here like to move

Final Thoughts

The Old Jail is proof that haunted places don’t need dramatic ruins or storm clouds hanging overhead. Sometimes the most unsettling places look warm and welcoming from the outside — like a pretty mask hiding broken teeth.

Behind those rosy walls is a story stitched with suffering, steel, and the echoes of people who never got to walk away.

And whether you believe in ghosts or not…
you’ll feel something watching.

Stay curious — and be careful what you look for in the dark. 🕯️

Keep it spooky. Leave the lights on.

Download our TMP Haunts Checklist — everything you need for your first ghost hunt.