Discover St. Augustine: 12 Fascinating Fun Facts About America's Oldest City

1. Florida or Bust

Before Pedro Menéndez de Avilés put St. Augustine on the map, we bet he muttered "Florida or Bust" under his breath: St. Augustine is the oldest permanent European settlement in the United States, dating back to 1565 when Spanish soldier Pedro Menéndez de Avilés founded the city, naming it after the saint whose feast day he first discovered the site on. Rich with history, this city has seen its fair share of bloodshed and battles, but today, it's all about Instagram-worthy Spanish colonial architecture and tourism.
Source => history.com

2. Gossiping Walls

In a classic case of "If these walls could talk, they'd have centuries of gossip to spill": St. Augustine's Castillo de San Marcos National Monument preserves the oldest masonry fortification in the continental United States! Completed in 1695 by the Spanish to defend Florida for their own siestas and fiestas, the fortress has withstood the barrage of time while safeguarding tales of more than 450 years of cultural mingling and intrigue.
Source => nps.gov

Did you know that Florida is home to one of the tallest lighthouses in the nation? Discover the Ponce de Leon Lighthouse, standing 175 feet tall with 203 steps, as it offers breathtaking views and a fascinating connection to the famous explorer. 🌊⚓️🔭

=> Fun Facts about Florida

3. Fountain of Youth's Untold History

What did the Native American say to the Spanish settler at the Fountain of Youth? "Been there, done that, got the arrowhead": St. Augustine's Fountain of Youth Archaeological Park was actually occupied by the Timucua tribe as early as 2,400 B.C., and later became the founding site of St. Augustine by Pedro Menendez de Aviles, featuring the earliest known remains of indigenous peoples' Christian burials in the U.S., as well as 16th-century Spanish structures and artifacts. Visitors today can experience a blend of history and fun at the park while boosting St. Augustine's economic and political scene, just as Walter Fraser envisioned.
Source => fountainofyouthflorida.com

4. Pirate Raid Reenactment

Arrrr matey, when St. Augustine residents decide to talk like pirates, they have more than a plunder of historical reasons to draw from: In 1668, Captain Robert Searle led a brutal, yet authentic, pirate raid on St. Augustine, killing 60 people and triggering the construction of the Castillo de San Marcos fortress. Today, locals don pirate garb and reenact this real-life Pirates of the Caribbean-esque tale in an annual event, much to the delight of history buffs and tourists with a swashbuckling spirit.
Source => hfm.club

5. Shh! It's the Narrowest Street

Why did the horse-drawn carriage refuse to enter the street? It couldn't fit! The uncanny truth about St. Augustine's Treasury Street: The U.S. might very well boast the narrowest street, thanks to the hushed whispers of pirates in the past. At under 7 feet wide, this slender lane was the secret passageway between Bay Street and the Royal Spanish Treasury, designed specifically to prevent carriage entry, and in turn, pirate raids during the 16th century.
Source => atlasobscura.com

6. Not Your Typical O'Reilly House

When someone tells you to go to the O'Reilly House, you might think of a jovial Irish pub trying to make you feel tipsy: However, in St. Augustine, Florida, the O'Reilly House is actually the Father Miguel O'Reilly House Museum, built in 1691—older than any Irish pub. Home to rich tales of Catholic tradition since 1565 that the Sisters of St. Joseph held on tightly to, you can explore this historical gem—sober—for free, from Wednesday to Saturday, between 10 a.m. and 3 p.m.
Source => floridashistoriccoast.com

7. The Old Senator Tree-Hugger

In a root awakening, the Old Senator stands tall as St. Augustine's very own "Woodstock" gathering place for history buffs and tree-huggers alike: This massive live oak tree, situated in the Howard Johnson Inn property, has witnessed centuries of life and lore with experts estimating its age to be several hundred years old. Though not the oldest tree in the city, its sheer size and accessibility make it a tourist favorite, and it remains healthy despite recent branch drops – thanks to arborist care and support poles.
Source => staugustine.com

8. Cheers to the Hidden Vineyard

Raise a glass and toast to Dionysus: in St. Augustine, you shall discover a hidden vineyard treasure! Behold: the award-winning San Sebastian Winery, which has triumphed over its competitors to claim bountiful gold, silver, and bronze medals at esteemed gatherings such as the Indy International and Florida State Fairs.
Source => kazzit.com

9. Haunted Lighthouse Hide-and-Seek

When you play hide and seek with ghosts, make sure to bring your Ecto Goggles and a proton pack: The St. Augustine Lighthouse in Florida is said to be haunted by the spirits of three drowned Pittee sisters and an unknown young African American girl, who met their untimely demise at the construction site in 1873, resulting in numerous paranormal accounts and even a chilling Dark of the Moon tour for those daring to join the girls in their eternal game.
Source => staugustinelighthouse.org

10. Cobblestone Conversations

If the cobblestones could talk, they'd probably need a lozenge: Aviles Street in St. Augustine isn't just ancient – it practically invented the word "vintage." Sauntering down the oldest street in the nation feels a bit like attending a Renaissance festival, but without the cringey accents and turkey legs: Originally known as Hospital Street in the 16th century, this charming brick pathway now boasts an abundance of artsy boutiques, eclectic galleries, and delicious eateries, all while proudly showcasing its historic roots at attractions like the Spanish Military Hospital Museum, General Kirby House, and Father O'Reilly House Museum.
Source => floridashistoriccoast.com

11. Plane vs. Speedboat

Before the Fast and the Furious was a glint in Vin Diesel's eye, St. Augustine hosted its very own race between an airplane and a speedboat in 1911: This historical city boasts a rich aviation past with movie sets at its airport, becoming a military gunnery range base during WWII, and eventually renewing its facilities for civil aviation at the Northeast Florida Regional Airport, now home to Northrop-Grumman's renowned aircraft maintenance services.
Source => flynf.com

12. Alcazar's High Society Shenanigans

Once upon a Flagler fortune: The lavish Lightner Museum in St. Augustine was originally the posh Hotel Alcazar commissioned by railroad tycoon Henry Flagler in the 1890s, boasting opulent Turkish and Russian baths, a high-stakes casino, and a swanky indoor swimming pool – quite the destination for high society shenanigans! Today, its ornate halls showcase everything from mesmerizing art and elegant architecture to curious bicycles and vintage tourism ads for guests who may be feeling just a tinge less extravagant.
Source => lightnermuseum.org