America’s Oldest City Survived 450 Years of Invasions While Preserving Its Spanish Soul in Florida

Welcome to St. Augustine, Florida

Most cities have a historic district. St. Augustine is history that happens to be a city. The Spanish built it in 1565, Henry Flagler turned it into a playground for the rich in the 1880s, and today it’s still evolving – though the cobblestones and coquina walls remain. Here are some interesting facts about the oldest, continuously inhabited city in America.

Named On an Auspicious Festival

St. Augustine got its name when Pedro Menéndez first saw land on August 28 on the feast day of St. Augustine of Hippo during a voyage.

The town has existed for about 450 years, longer than any other Euro town in the whole U.S., and was picked since it had fresh water close by.

Original Founders Were Diverse

Menéndez started St. Augustine in 1565 with a fleet of 600 souls which included farm folks, priests, skilled hands, and crews from ships.

This first group dealt with bug bites, bad storms, and fights with first settlers. But together, they made St. Augustine a key town in the south for 300 years.

Most of the first homes were small, wooden structures with palm leaf roofs. The first town plan was set up with a big square in the heart and roads in a grid system.

The first mass in the new world was said right here too.

America’s First Free Black Settlement

Fort Mose, set up in 1738 just north of town, was the first place where Black folks could live in peace, free by law. Folks who fled slave farms found safe haven here.

The fort stood as the first stop on a south-bound path and had a strong Black force led by Francisco Menéndez, who was born in West Africa. But when the Brits took charge in 1763, most of those who lived here fled to Cuba.

Digs at the site have revealed old gun flints, smooshed slugs, belt clasps, clay pots, burnt seeds, and food bones as proof of the settlement.

Famous Creative Minds Lived Here

Famed Civil War boss Kirby Smith grew up in this town, and Jacob Lawrence, the great Black painter, trained with the Coast Guard in World War II.

Gamble Rogers called this town home and even Mark Twain spent time at the grand Ponce de Leon Hotel, finding muse in the scenery.

Plus, Marjorie Kinnan Rawlings of “The Yearling” fame drew much of her work from the rich woods and lakes near here.

The most recent creative mind? Remember legend Ray Charles, the blind soul star. He lived in St. Augustine and made his mark on the town’s sound.

America’s Skinniest Street

Treasury Street links the bay to the old Royal Spanish Treasury and was built slim on purpose to stop thieves from looting and running.

The real width is only 6 feet, 1 inch at its most narrow point, which dates back to the 1600s when most streets in town were built tighter.

Old pics from the 1900s show two men with arms spread could touch both sides. Folks still walk this slim path each day, and it’s now a top spot for fun pics.

Find it right by Bay Street, next to where the old town trolley stops.

The Famed Fountain of Youth (Not Literally)

Fountain of Youth site was home to Timucua tribes for nearly 3,000 years before any ships from Spain showed up, and there’s plenny of proof.

Recent digs have found over 4,000 Native burials there, plus rare items like Spanish glass beads and silver pieces. The spring still flows, and you can drink from it.

The park sits on 15 lush acres overlooking the bay and St. Augustine Inlet. Today, you can watch live shows where they fire old guns and show how folks lived back then.

The Love Tree’s Natural Romance

In the heart of town stands a palm tree that’s grown right through a live oak tree. Town tales claim that pairs who kiss here will love each other for good.

The odd plant mix can be found at 6 Cordova Street. Some say these trees chose to grow as one, while others think seeds from bird poop made this quirk.

No one knows for sure when the trees first grew this way. But lots of folks come to get hitched here, and some say if your love dies, the trees will split as well.

The Lighthouse’s Tragic Backstory

The St. Augustine Lighthouse (the fifth most haunted spot on earth) has stood watch since the 1500s and seen much death.

The most popular ghosts are the Pittee girls who drowned in 1873 at sea. Guests hear children laughing and see wet prints that won’t wipe off.

The tower stands 165 feet tall with 219 steps to climb to the top. It still works as a guide for ships with its big lens made of 370 hand-cut glass prisms.

The Toad Fountain Tells Time

Henry Flagler’s vast cash helped shape all of the state, but his best work sits at the ground gates of Flagler College, near a big stone basin.

The stone toads show what time it is by how they’re placed. The front yard showpiece is one of the few in the world, as most rich folk chose sun dials or clocks.

The school was once the Ponce de Leon Hotel with a big roof space made from stained glass by Louis Tiffany. The whole place cost $2.5 million to build in 1888.

Funeral Home to Spooky B&B

Casa de Suenos is now a cute B&B, but it was once a thriving death care store. The place still has its stone floors and curved doors from 1904.

The old death house stands at 20 Cordova Street and folks say the souls of those who passed through on their last trip still hang out.

The main ghost is thought to be the first boss who owned it in death trade times. Some folks stay there just to try to see or feel weird stuff go on.

Old Jail is Super Haunted

Henry Flagler built the town’s jail in 1891 to hold up to 72 men, both whites and blacks, in their own parts till 1953.

The jail looks quite nice from the road, with pink walls and nice trim, but it has a terrible history. At least eight men were hung from the rope posts out back.

Night guests hear chains, moans, and steps on the wood planks with no one there. One ghost, named Charlie, still haunts the place.

Now ghost hunts here start at dark and run for 45 chilling minutes.

Matanzas Bay Has a Bloody Past

The calm bay that hugs the town has a name that means “killings” in the Spanish tongue, a when Spain’s troops killed all the French folks they could find.

The grim tale lives on in the name of Fort Matanzas, a small stone fort south of town built to guard a back way in that a foe used to sneak up on the town in the past.

The town bridge of lions stands guard. Some say the seas here can look blood red at night when the moon hits them just right.

Visitor’s Guide & Other Information

Contact / Help: 904-825-1000 (for free trip planning assistance)

Address (Main Help Desk): 10 S. Castillo Drive, St. Augustine, FL

Access Points / Route: Start at the main help desk; Old Town is the best base for walking to nearby attractions

Ways to Travel/Transit:

• Hop-on, hop-off cart tours (best for avoiding parking issues)
• Many B&Bs offer free shuttles to the beach
• Free parking available next to the help desk

Timings: Most attractions open daily from 9:00 AM to 6:00 PM

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