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Old City Walk

In production St. Augustine, FL📍 9 stops🚶 3.6 km loop⏱ ~70 min

⚠️ AI-generated tour, not yet walk-tested. Spot something wrong? Tell us.

Welcome to St. Augustine, the oldest continuously occupied European settlement on the U.S. mainland, founded by Spain in 1565. This loop visits a 17th-century coquina fort, an old wooden schoolhouse, the city's historic cathedral and governor's house, Henry Flagler's Gilded Age hotels, a territorial-era boarding house and the Bridge of Lions.

Stop 1 of 9Free preview

Castillo de San Marcos

Castillo de San Marcos, on Matanzas Bay

Welcome to St. Augustine, and to the Castillo de San Marcos, the oldest masonry fort in the continental United States. Spanish Admiral Pedro Menéndez de Avilés founded the city in 1565. After Sir Francis Drake's attack in 1586, nine wooden forts followed.

Then in 1668, the English privateer Robert Searles raided the town and burned much of it, and Spain decided to build in stone. Construction began on October 2, 1672, to a design by the engineer Ignacio Daza, and the core of the fort was finished in 1695. It's built of coquina, a stone made of ancient shells bonded together, quarried across the bay on Anastasia Island. The star-shaped fort was attacked several times and besieged twice, in 1702 and 1740, but it was never taken by force.

It changed hands five times, always peacefully. Under U.S. control it served as a military prison for Native Americans, including the Seminole war chief Osceola and members of Geronimo's band. The fort's original name was restored by Congress in 1942.

🚶 Walk to the next stop (370 m · ~5 min walk): Walk west toward the old City Gate and onto St. George Street. The Oldest Wooden School House is at number 14. About 5 minutes.

Sources: en.wikipedia.org › Castillo_de_San_Marcos · wikidata.org › Q101094405

Stop 2 of 9Free preview

Oldest Wooden School House

Oldest Wooden School House, 14 St. George Street

This little building at 14 St. George Street, near the city gate, is known as the Oldest Wooden School House. It's promoted as the oldest wooden school building in the United States, though that claim is disputed. It wasn't used as a school until 1788, and a schoolhouse in Portsmouth, Rhode Island, was built as a school back in 1725.

The exact date this building went up is unknown, but it first appears on tax records in 1716. No wooden buildings in St. Augustine survive from before 1702, when the British burned the city. Look at the large chain wrapped around the house.

It was put there in 1937, to help anchor it to the ground in a hurricane. The walls are bald cypress and red cedar. The schoolmaster and his family lived upstairs, above the classroom, and the kitchen was in a separate building, to cut down on heat and the risk of fire. The classroom was one of the first in the country to be co-ed, teaching both boys and girls from 1788.

🚶 Walk to the next stop (550 m · ~7 min walk): Walk south down St. George Street to the Cathedral Basilica, on Cathedral Place. About 7 minutes.

Sources: en.wikipedia.org › Oldest_Wooden_School_House · wikidata.org › Q7085575

All stops

Route: OSRM foot profile (routing.openstreetmap.de), Map data © OpenStreetMap contributors. Narration audio: generated with the free Piper text-to-speech voice (prototype voice). Times are estimates.