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St. Augustine at 250: America’s oldest city still has stories to tell

ST. AUGUSTINE, Fla. – You can’t celebrate 250 years of American history without starting with the nation’s first city — St. Augustine, Florida.

The city hums with tourism, culture and a blend of influences that spans centuries.

Friday News4JAX visited the Oldest House at 14 St. Francis St., where Charles Tingley, Senior Research Librarian and Historian at the St. Augustine Historical Society, spent nearly two hours walking him through more than 450 years of history.

“There is layer upon layer of history here,” Tingley said.

From founding to fort

Spanish explorer Pedro Menéndez de Avilés founded St. Augustine on Sept. 8, 1565 — making it the oldest continuously occupied European settlement in the United States. By 1586, English privateer Sir Francis Drake had already attacked it. Through it all, the city held.

To protect Spain’s treasure fleets — which carried gold, silver and emeralds from the New World back to Europe along the Gulf Stream — Spain built the Castillo de San Marcos.

It remains the oldest masonry fort in the United States.

“Having a strong fortification kept Florida in Spanish hands,” Tingley said.

Funding the operation wasn’t what most people would expect, either.

“I bet you can’t possibly guess where the money came from that paid for all the soldiers and politicians here in St. Augustine,” Tingley said. “It was the taxes on the city of Puebla, Mexico.”

Flags, loyalists, a new nation

Florida changed hands not through battle, but through a bargain — traded from Spain to Britain in 1763 in exchange for Cuba. When the American Revolution began, loyalists poured in.

“The population of St. Augustine during the American Revolution swelled from 2,000 to about 10,000,” Tingley said.

Spain reclaimed Florida in 1784. The United States took possession in 1821 — and the layers of history kept building.

Nowhere else like it

Visitors feel it the moment they arrive.

For Tingley, that depth is more than visual — it’s literally underfoot.

“In downtown St. Augustine, there is two to three feet of cultural deposit wherever you walk — layer after layer, strata after strata, of the physical evidence of people living on this site,” he said.

For more on St. Augustine’s history and Charles Tingley’s research, you can click on this link to this website.