EIGHT MEN HANGED HERE: The Old Jail That Henry Flagler Built to Look Like a House

By Staff Reports

🌙 FLORIDA AFTER DARK — It looks like a charming Victorian house on San Marco Avenue. It was built to look that way — because Henry Flagler didn’t want his hotel guests looking at a jail.

St. Augustine’s Old Jail was built in 1891, funded with $10,000 from Flagler himself, who wanted the county jail moved away from his luxury Ponce de Leon Hotel. So the P.J. Pauley Jail Company — the builders who would later build Alcatraz — constructed a maximum-security jail disguised as a Romanesque Revival home. It served as the St. Johns County Jail from 1891 to 1953.

Inside the pretty facade: up to 84 prisoners, as many as four to a cell, no indoor plumbing until 1914, open barred windows, a death row cell — and a gallows in the compound where eight men were executed during the jail’s years of operation. Disease killed inmates who never finished their sentences. The building is now on the National Register of Historic Places and operates as the Old Jail Museum.

The reported hauntings write themselves from that history: chains rattling, footsteps in empty cell blocks, voices where no one is standing. Tour guides have told those stories for decades, and the jail’s “haunted” reputation is now as much a part of St. Augustine as the building itself.

Join the conversation: Have you walked the Old Jail at night — and heard something? Florida After Dark wants your stories: send them to tips@floridachatter.com and yours could be our next feature.

Sources: Old Jail Museum / St. Augustine Old Jail official history; Historical Marker Database (HMdb); National Register of Historic Places.

Photo: Excel23, via Wikimedia Commons (CC BY-SA 3.0).