Old Jail

Built in 1891 by Henry Flagler to serve as the city's prison for nearly 60 years. The building housed hardened criminals alongside the sheriff and his family, who lived under the same roof across from the prisoners they watched.

The Old Jail in St. Augustine operated from 1891 to 1953, housing some of the era's most dangerous criminals within its 20-foot-high walls. Built at Henry Flagler's insistence—he didn't want his luxury hotel guests viewing a jail—the imposing structure now ranks among the most haunted buildings in America and is listed in the National Directory of Haunted Places.

Sheriff Joe Perry ruled the jail with an iron fist. Standing 6'5" and weighing 300 pounds, his imposing presence instilled fear and respect among inmates. His spirit is said to linger, with visitors reporting his ghostly apparition wandering the corridors.

Eight men were executed on the gallows during the jail's operation. Charlie Powell's botched hanging was particularly gruesome—the inefficient execution resulting in a slow, agonizing death. His spirit reportedly remains, conversing with visitors who pass through.

Conditions were deplorable. Windows had no glass, concrete and metal created a cold, sterile environment, and mattresses stuffed with Spanish moss harbored red bugs. No blankets or pillows were provided. A doctor only visited during hangings to pronounce the executed dead, so illness and untreated maladies claimed many lives.

Maximum security cells included stockades, a torture cage, and a clear view of the execution area—psychological torment added to the physical.

Paranormal activity permeates the building. Wailing and moaning emanate from maximum security and solitary confinement. A little girl's voice has been heard in the sheriff's quarters, where his family lived. Whistling, dastardly laughter in the women's cells, and the tune of "Swing Low Sweet Chariot" drift through empty hallways. Footsteps accompanied by the clink of chains suggest inmates still shuffle through the cell blocks. An entity called "The Crawler" reportedly moves along cell floors, following visitors.