Old Jail

Henry Flagler built St. Augustine's jail to look like a house — because the real jail was too close to his hotel. In 1891, with the Ponce de Leon Hotel redefining the Ancient City as a Gilded Age resort, Flagler funded a new county jail on the condition that it not look like one: Romanesque Revival, Victorian facade, a building guests could walk past without remembering that St. Augustine had criminals. The Pauly Jail Company — the same firm that built Alcatraz — did the work.

Inside it was a jail, and a hard one. The sheriff lived in the front of the building with his family — his wife cooked for the prisoners, his children grew up across the hall from the cells — and the gallows stood in the yard. Charlie Powell, the most notorious inmate, was reportedly hanged there twice — the first rope broke. The jail held murderers, rustlers, and everyone St. Augustine wanted out of sight for sixty-two years, until the county built a real prison in 1953.

It became a tourist attraction the year after it closed — the 'Authentic Old Jail,' cells preserved, sheriff's quarters intact, the gallows still standing. It's been on the ghost-tour circuit for decades: footsteps in the sheriff's quarters, the cell doors that close on their own, the usual inventory. The building's real distinction is architectural — a jail designed to disappear into a resort town, by the man who decided what St. Augustine was allowed to look like.