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What's the Oldest City in America?

Ellen Gutoskey
St. Augustine's Flagler College—originally the Ponce de León Hotel, constructed in 1888.
St. Augustine's Flagler College—originally the Ponce de León Hotel, constructed in 1888. / Wolfgang Kaehler/GettyImages
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Jamestown may have earned the distinction of being the first permanent English colony in North America when it was settled in 1607, but it’s not the oldest city in the U.S. That title is generally given to St. Augustine, a city on Florida’s eastern coast about an hour’s drive southeast of Jacksonville.

In July 1565, Spanish conquistador Pedro Menéndez de Avilés set off for Florida with 11 ships, some 2000 sailors, and a directive from King Philip II to defend Spain’s coastal holdings against French encroachment. On September 8, Menéndez de Avilés alighted on a stretch of land that he had first spotted on August 28—the feast day of St. Augustine of Hippo. He promptly claimed the area for his country and christened it after Augustine, the patron saint of printers, theologians, and brewers (he’d been a bit of a party guy before finding his holy vocation).

Print of Pedro Menendez de Aviles
Pedro Menéndez de Avilés plotting his legacy. / Historical/GettyImages

Menéndez de Avilés and his cohorts paid homage to their Catholic roots in another way, too: by holding Thanksgiving mass the very same day they disembarked on the shores of Florida. This was followed by a meal shared with the Timucua—a Native American people who had called the region home for thousands of years before the Spaniards showed up. 

Through war and disease, European settlers would obliterate the Timucua within the next few centuries. But on September 8, at least, proceedings were peaceful; and the communal banquet is sometimes cited as America’s first “true” Thanksgiving (though it’s worth noting that the Timucua had also feasted with French explorers more than a year earlier). St. Augustine’s head settler wasted little time in moving against the French, brutally slaughtering the inhabitants of Fort Caroline just 12 days after he landed in Florida.

painting of timucua villagers at the u.s. capitol
A painting of Timucua villagers exhibited in the U.S. Capitol. / USCapitol, Flickr // Public Domain

Though Menéndez de Avilés was far from the first European to stake out territory in what is now the U.S.—or even Florida—the fact that St. Augustine has been continuously occupied since 1565 lends credence to the claim that it’s the nation’s oldest city. Its age is reflected in the historic nature of some of today’s popular tourist spots, like the Castillo San Marcos, the continental U.S.’s oldest existing masonry fort. There’s also Ponce de León’s Fountain of Youth, an archaeological park where you can learn all about St. Augustine’s early days and the Timucua history that came before it.

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