Old Jail Museum, St. Augustine

The Old Jail Museum in St. Augustine is a historical landmark that has stood the test of time. It was built in 1891 by Henry Flagler, an oil magnate and industrialist who had made significant real estate investments in the area, including the construction of the Hotel Ponce de Leon. The jail was built just north of downtown on San Marco Ave and was disguised so as not to create an eyesore that would strike fear in the hearts of the general public and discourage Flagler's wealthy friends from investing in the city.

The Old Jail served as the St Johns County Jail until 1953, after which it was sold to entrepreneur Henry "Slim" McDaniel, who began operating it as a roadside tourist attraction. It was eventually added to the U.S. National Register of Historic Places in 1987 and is now a museum that showcases the harsh living conditions of the inmates who once lived there.

The two-story northern wing of the Jail consists of a general population and maximum security area, a women's section, and a lower level kitchen. Maximum Security was used to house the most dangerous prisoners and even had a Death Row cell for those condemned to die. The overall conditions at the Jail were poor by modern standards, with prisoners typically used as free farm laborers during the day. Baths were infrequent, toilet facilities consisted of one bucket per cell, and the diet was poor. Segregation by race was strictly adhered to, and disease, violence, and death were commonplace. Eight men were hung from the Gallows on the Jail compound during its history.

The Old Jail Museum is a restored jail with sheriff's living quarters that houses a display of weaponry and a pictorial history of the hangings carried out at the Old Jail, with emphasis on the time the Sheriff CJ Perry was in residence with his family. Visitors can only access the Jail by guided tour, with costumed guides "processing" in new prisoners. The Jail also serves as the grand finale to Old Town Trolley's Ghost and Gravestones tour, allowing visitors to access the building by night as well.