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Old Town Trolley Tours® of St. Augustine Route Map & Stops
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Trolley Stop
stop 1 - New England Aquarium and Faneuil Hall Marketplace

  The Old Jail
  St. Augustine History Museum
  Gator Bob's Trading Post
  Oldest Store Museum Experience
  Free Parking
  Trolley and discount attraction tickets
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Complete Guide To The Old Jail in St. Augustine

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st augustine old jail

A Tour Through History

Located on San Marco Avenue in St. Augustine’s Uptown District, the Old Jail Museum offers an educational and intriguing look into what it would have been like to be a prisoner in the Nation’s Oldest City. Take a guided tour led by the “jailers” for a compelling look at the cells where imprisoned men and women once lived, the maximum security area reserved for the most nefarious criminals and a collection of weapons.

gallows at old jailVisitors can also take a look at the cell blocks, gallows and sheriff’s quarters. See where the sheriff, his wife and children lived, right upstairs from the prisoners, and how they used their own kitchen to prepare meals for the inmates. A tour through this attraction will show visitors what life was like as an inmate and how the Old Jail helped shape St. Augustine’s history.

Correcting an Eyesore
Built in 1891 by P.J. Pauley Jail Building and Manufacturing Company out of St. Louis, Missouri, the construction was actually financed in part by railroad magnate Henry Flagler. Flagler struck a deal with the county for $10,000 to build a new jail because the existing structure sat on land that he needed to erect his Ponce de Leon Hotel. Flagler also didn’t want the community’s most undesirable inhabitants to be near his hotel and esteemed guests.

Built in Romanesque Revival style, the Old Jail, which was added to the U.S. National Register of Historic Places in 1987, was intended to house up to 72 prisoners. The two-story northern wing consisted of the general population, maximum security, women’s section and a lower kitchen level.

Despite the outside architecture, overall conditions at the facility were notoriously bad. An arrest in St. Augustine was pretty much a death sentence with time served at the Old Jail, especially with America’s most feared sheriff, Joe “CJ” Perry, at the helm.

60 Years of Service
For nearly 60 years - until 1953 - the Old Jail served as the St. Johns County facility for petty thieves and hardened criminals. There were even eight recorded executions, two of which were accused murderers. Sim Jackson, who was hanged in 1908 after murdering his wife with a straight razor, is among the group.

The Well Known Sheriff
Today, visitors learn about the infamous Sheriff Perry, who served from 1889 until 1897 and again from 1901 until 1919. His stature as a “big, bold man” at 6’6” and weighing 300 pounds was intimidating even for the most hardcore of inmates. Though popular in the community, Perry was feared amongst cell inhabitants - both male and female - for his reputation of renting out prisoners to local farmers through a leasing system.

Paranormal Activity
As part of Old Town Trolley’s Ghosts & Gravestones tour, visitors can also check out the Old Jail at night and perhaps catch a glimpse of the paranormal activity that has been reported over the past century. One such figure has been deemed “The Crawler,” an effigy that low crawls on the floor of the main cell block, following people.

So make sure to set some time aside on your next St. Augustine adventure as the Old Jail deputies entertain you with tales of justice and punishment when Florida was America’s southernmost frontier. Just be thankful that you’re standing on the other side of the big house.

Nearby Attractions

St. Augustine History Museum
couple at st augustine history museumHenry Flagler was a powerhouse and catalyst for change in the real estate and transportation industries. His contributions to Florida are documented and displayed throughout the St. Augustine History Museum. As you tour through, you’ll also see authentic artifacts, unpublished photographs and learn about the evolution of St. Augustine and Florida under Spanish and British rule. More than 400 years of history is on display including toys and dolls from the early 19th and 20th centuries, a replica of a Spanish galleon and real gold, silver and jewelry found in lost treasures off the Florida coast. Housed on the Old Jail, the museum offers another level of insight into Florida’s past. FREE Admission with purchase of Old Town Trolley Ticket

Gator Bob's Trading Post
Gator Bob's Trading Post offers a wide variety of t-shirts, souvenirs, gator heads, cold drinks, post cards, jewelry and more. And coming soon will be an old-fashioned arcade and snack area.

Oldest Store Museum Experience
oldest store museum and cast memberWatch in amazement as our friendly clerks, butcher and Snake Oil salesman demonstrate the very latest inventions for turn-of-the-century living. Step back in time and discover the latest and best time saving miracles from 1900! Items such as a goat-powered washing machine and a gas powered iron! It’s truly like walking into a Sears Roebuck catalog from 1908. From steam-driven tractors, tonics, worm syrup, guns, bikes and so much more.

Go to St. Augustine Hotels and Bed & Breakfasts


Related Articles:
St. Augustine Historic Sites
St. Augustine Attractions
Reasons To Visit St. Augustine

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Saint Augustine’s Best Tour to See the Spanish Quarter, Flagler Memorial Church, the Bay View, St. Augustine Old Jail,
Plaza de la Constitucion, San Sebastian Winery, Lightner Museum, Castillo de San Marcos, Fountain of Youth, and Much More!

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Old Town Trolley Tours and Transportainment are registered
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