Old Jail – St. Augustine

One of St. Augustine’s kitschy attractions is housed in a historic building that is part of the insiders story of the ancient city.

Long known for its roadside attraction feel and attitude, with “fun” displays such as a working gallows, a dunking pool for drunks and a large collection of cattle horns, the Old Jail can be first connected with the St. Augustine (and later Palm Beach and Miami) developer Henry Flagler.

Flager’s fantastic Hotel Ponce de Leon, the first grand resort built in Florida, opened in 1888. Due to his connections in high society, wealthy New Englanders quickly started to spend their winters in St. Augustine. As St. Augustine grew into an elite resort, Flagler realized that there was one issue to address (at least in reference to this story). The existing St. Johns County Jail was not up to his standards visually and perhaps structurally.

It’s unclear as to Flagler’s complete reasoning, but it appears that he was in favor of a modern jail that was secure, attractive and located out of the center of town. Working directly with the county, Flagler financed the construction of the new jail and it was built at the edge of what is typically considered the old city area, north of the Castillo de San Marcos.

Reportedly spending $10,000 of his own money, Flagler contracted with P. J. Pauly, Sr. and the Pauly Jail Building Company of St. Louis, Missouri, a firm that would go on to become one of the more successful jail construction companies. The Pauly Company both designed and built the jail in a Romanesque Revival style that appears more as a hotel or house than a jail. The construction was completed in 1891.

With its current headquarters in Noblesville, IN, the Pauly Jail Building Company is the nation’s oldest correctional facilities contractor. Started in 1856, P. J. Pauly and his family worked as Mississippi steamboat blacksmiths. Eventually they began to design and build steel cages that could be mounted on wagons to create portable jail cells for the rapidly growing nation.

Expanding into buildings, they built many 19th and 20th century jails and correctional facilities around the country, including several which are on the National Register of Historic Places. This includes the Old Hamilton County Jail in Jasper, FL (listed in 1983) which is currently the home of the Hamilton County Historical Museum.

The Pauly Jail Building Company is still building correctional facilities and as of 2020, P. J. Pauly, Sr.’s great-great-grandsons continue the family tradition by guiding the company.

The St. Johns County Jail continued to be used until 1953, when the county built a new facility. The building was sold to Henry McDaniel who turned the building into a roadside tourist attraction called the Old Jail. Better known as “Slim”, he created a museum and attraction unlike any other in Florida.

The Old Jail focused on forms of punishment from the past, some which were/are rather creatively presented. There was the dungeon for solitary confinement, the whipping post, the sweat box and the large gallows where, it was said, “three men were hung” in an early brochure. The attraction also had a gun collection, which were supposedly used in crimes and, as a bit of a western flair, large collections of cattle horns and cactus.

By the 1960s, the attraction was also associated with a tour company that led tours around the old city in “trains” or “trolleys” that were actually a Jeep or other truck which pulled a series of cars that could accommodate around 50 people. The connection with tour trains continues to this day and is known as the Old Town Trolley. It’s one of two similar tour companies operating in St. Augustine.

The building was added to the National Register of Historic Places in 1987. It continues to be one of the more popular attractions in the city. It’s located just outside of the old city environs, near the Fountain of Youth, Ripley’s Believe it or Not and the Mission Nombre de Dios, and like all those attractions, it has its own parking lot. That’s an advantage if visitors want to ride the Old Trolley because they can get free parking for the day.


The help provided by Melissa Miller of the Pauly Jail Building Company is appreciated.

Old Jail Postcards

Old Jail Brochure 1956

Old Jail Brochure 1958

Old Jail Brochure c1968