The Old Jail Museum in St. Augustine, Florida, offers a captivating glimpse into the city's past, showcasing the stark realities of 19th and early 20th-century incarceration. Constructed in 1891 by the P.J. Pauley Jail Building and Manufacturing Company, with funding from industrialist Henry Flagler, the jail was designed in the Romanesque Revival style to blend with the city's aesthetic and avoid deterring tourists. Operating until 1953, the facility housed up to 72 prisoners in conditions that were harsh by today's standards, including overcrowded cells, minimal sanitation, and the use of inmate labor. Notably, eight executions were carried out on the premises during its operational years. Today, visitors can explore the restored jail through guided tours led by costumed interpreters who bring to life the stories of inmates and the notorious Sheriff Joe Perry. The museum also features exhibits on the evolution of the justice system and offers "Old Jail After Dark" tours for those interested in its haunted history. Located at 167 San Marco Avenue, the Old Jail Museum stands as a significant historical site, reflecting the complexities of law enforcement and penal practices in America's oldest city.