Uptown St. Augustine

You’ve shopped, explored, and eaten your way through the Historic District of Downtown St. Augustine. Go north! Uptown St. Augustine is home to some of the city’s greatest attractions, dinner spots, and even more shopping. Read on for a small selection of what you can find in Uptown.

Fountain of Youth

The Fountain of Youth Archaeological Park is a must-see for visitors to the Nation’s oldest city. The 15-acre park is equal parts fun and educational, with canon firings, guides in period costumes, and free-roaming peacocks. Since 1868, guests have been invited to learn about the park’s history via significant archaeological discoveries like artifacts, burial grounds, original Spanish structures, and information about the Timucua Natives that occupied the area before the Spanish fleets came ashore. Founder’s Riverwalk is a 600 foot boardwalk featuring a spectacular view spanning miles in all directions, to give you a sense of what Spanish settlers saw upon landing.

            For a nice treat after your visit, stop by Fountain of Juice conveniently located just outside the park gates! Since 1955, Fountain of Juice has served fresh squeezed lemonade, fruit smoothies, and coffee every Saturday and Sunday from 9am-5pm. Enjoy a leisurely walk down Magnolia Avenue under a canopy of live oaks, one of America’s most photographed streets.

The Old Jail

            Don’t let the charming pink facade fool you! The Old Jail housed some of Florida’s most dangerous criminals. Costumed deputies tell vivid tales while guiding visitors through cell blocks, sheriff’s living quarters and office, “death row,” and the gallows. The Old Jail also offers haunted evening tours for the brave of heart.

            The history of this old prison is more fascinating than you’d expect.  Made to hold up to 72 prisoners, this jail was funded by railroad magnate Henry Flagler after striking a deal with the county to move the existing jail to make room for the Ponce de Leon Hotel. The St. Johns County Jail - Constructed by the same company that built San Francisco’s Alcatraz -  was intended to have curb appeal so visitors would feel comfortable staying at Flagler’s luxurious hotel roughly one-and-a-half miles away. The site served as the county jail between 1891 to 1953 and became a tourist attraction one year later. The building has been preserved and restored to its former glory and has held a spot on the National Register of Historic Places since 1987.

Ripley’s Believe It or Not! Museum

            A true St. Augustine staple, Ripley’s Believe It or Not! is home to bizarre items from all over the globe. A day full of fun is guaranteed with 800 exhibits ranging from real shrunken human heads, optical illusions, and incredible art works crafted from mediums like shredded money, keyboard keys, matchsticks, soda cans, and so much more!

            Formerly known as Castle Warden, the Moorish Revival building was constructed of poured concrete in 1887 for William G. Warden, a prominent resident and former partner of John D. Rockefeller and Henry Flagler of Standard Oil. The home was renovated into a hotel in the 1940s by Pulitzer winning author Marjorie Kinnan Rawlings and her husband Norton Baskin. Robert S Ripley, the illustrator famously known for his “Believe It or Not!” cartoons, was convinced the castle was perfect for his macabre collection. He was unable to complete the purchase but in 1950, one year after his death, Ripley’s estate managed to secure the building and establish the first Ripley’s Believe It or Not! Museum.

Uptown Lodging

            Originally the carriage house for the Wardens, Castle Garden is now a cozy bed and breakfast that looks like a miniature version of Castle Warden. Located just behind Ripley’s, it’s the perfect spot between Uptown and Downtown, just a short walk away from the Castillo de San Marcos.


Uptown Dining

            When it comes to good food, you’re spoiled for choice in Uptown. Find anything from wine tastings to fine dining, comfort food, and more.

Carrera Wine Cellar

            Stop in and browse Carrera Wine Cellar’s large selection of wines. Enjoy a glass alongside a tasty charcuterie board, Bavarian pretzels and more on their patio or in the cozy lounge. Looking for gifts or souvenirs? Bottles and cases are available for purchase. Check their website for details on classes, packages, and events.

The Raintree Restaurant

            Since 1981, The Raintree has been nationally and internationally recognized for its award-winning menu. Enjoy casual fine dining on the welcoming front patio or inside the sunroom of the 1879 Victorian building. To make the experience even sweeter, guests can take in the stunning view of the Mission Nombre de Dios just across the street.

Uptown Swinery

            Who doesn’t love comfort food? Uptown Swinery is described as a Southern public house serving up American comfort classics with a farm-to-table experience. Locally sourced ingredients are the cornerstone for the brunch and dinner menu which celebrates all things pork! Enjoy your meal on the deck or sit inside and enjoy live entertainment from local musicians.

Post Date

June 23, 2020