St. Augustine Trivia
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50 free St. Augustine trivia questions with answers — history quiz, new questions added Aug 2026.
40 free St. Augustine trivia questions with answers. St. Augustine, Florida, has been continuously inhabited since 1565, which makes it older than Jamestown, Plymouth and every other European settlement in the contiguous United States. This quiz walks its 460 years: Pedro Menéndez de Avilés and the feast day that gave the town its name, the massacre at Matanzas Inlet, Sir Francis Drake's raid, the coquina walls of the Castillo de San Marcos that swallowed British cannonballs, Fort Mose and the first free Black settlement in America, twenty years of British rule, Osceola in Fort Marion, Henry Flagler's Ponce de Leon Hotel wired by Thomas Edison, the Bridge of Lions, the lighthouse and the summer of 1964 when Martin Luther King Jr. was arrested on the steps of the Monson Motor Lodge. The last stretch turns to the saint himself: Augustine of Hippo, his mother Monica, the Confessions, The City of God and the siege in which he died. Easy questions ask which country founded the city and what the old fort is made of; the hard ones want the year the Castillo was finished, the pirate who raided the town in 1668 and the Latin phrase behind Augustine's conversion. Every answer was checked against Wikipedia's articles on the city, its landmarks and the saint, and each question carries the sentence that supports it.
30 of 50 questions with answers and explanations. Play the quiz
Q 01A Mass and shared meal at St. Augustine's founding in 1565 is often called America's first what?
Thanksgiving
Thanksgiving. The settlers came ashore on September 8, heard Mass and then fed the local Seloy people, 56 years before the Pilgrims sat down at Plymouth.
Q 02Which Spanish admiral founded St. Augustine on September 8, 1565?
Pedro Menéndez de Avilés
Pedro Menéndez de Avilés was sent by Philip II to drive the French from Florida; within two weeks of landing he marched overland through a storm and took their Fort Caroline at dawn.
Q 03Why did its Spanish founders name St. Augustine after that saint?
Land was sighted on his feast day
Land was sighted on his feast day, August 28, 1565. The fleet then spent eleven days working up the coast and confronting the French before the settlers came ashore and named the town.
Q 04Which continuously inhabited city under the US flag is older than St. Augustine?
San Juan, Puerto Rico
San Juan, Puerto Rico, was founded by the Spanish in 1521, which is why St. Augustine's claim to be the oldest city is worded to cover only the contiguous United States.
Q 05Which Native people lived in the village of Seloy, where the Spanish founded St. Augustine?
Timucua
Timucua. Their chief Seloy's village stood where the Spanish landed; the Seminole, Florida's best-known tribe, only took shape in the 1700s, when Creek bands moved south.
Q 06What does 'Matanzas', the name of the inlet south of St. Augustine, mean in Spanish?
Slaughters
Slaughters. In 1565 the Spanish put to death most of the shipwrecked French soldiers who surrendered on its shore, sparing only a few, and the name has stuck ever since.
Q 07Which English privateer sacked and burned St. Augustine in 1586?
Sir Francis Drake
Sir Francis Drake was sailing home from raiding the Spanish Caribbean; when the Spanish rearguard killed his sergeant major, he ordered the whole town razed to the ground.
Q 08The Castillo de San Marcos is built from what local stone?
Coquina
Coquina was quarried across the bay and ferried to the site, where Native labourers from the missions and masons brought from Cuba raised the walls.
Q 09Why did British cannon fire barely damage the Castillo de San Marcos?
Its soft shell stone absorbed the shot
Its soft shell stone absorbed the shot: cannonballs sank into the walls and stuck instead of shattering them, so the walls held firm through the sieges of 1702 and 1740.
Q 10Which agency has looked after the Castillo de San Marcos since the War Department handed it over in 1933?
The National Park Service
The National Park Service has run the fort ever since. In 1942 Congress gave it back its original Spanish name, in honour of its Spanish history, after more than a century under an American one.
Q 11A lone US sergeant once handed over the never-conquered Castillo de San Marcos, demanding only a receipt from whom?
Florida militia
Florida militia. In January 1861, three days before the state seceded, Sergeant Henry Douglas, the fort's entire garrison, gave up the keys only once they had signed for the fort and its contents.
Q 12Under American rule the Castillo de San Marcos was renamed for which Revolutionary War hero, nicknamed the Swamp Fox?
Francis Marion
Francis Marion's name went on the fort after the US Army took it over from Spain; as Fort Marion it went on to hold Seminole, Plains and Apache captives.
Q 13Plains warriors jailed in St. Augustine's fort in the 1870s became known for which kind of drawing?
Q 21Carrère & Hastings, architects of the Ponce de Leon Hotel, later designed which Manhattan landmark guarded by marble lions?
The New York Public Library
The New York Public Library. The two young partners won its design competition in 1897; the St. Augustine hotel, a decade earlier, had been their first big job, landed through Hastings's father.
Q 22Since 1968 the old Ponce de Leon Hotel has been the centrepiece of which institution?
Flagler College
Flagler College opened in 1968, a year after the hotel closed, and its students now eat in the old dining room beneath dozens of Louis Comfort Tiffany stained-glass windows.
Q 23The St. Augustine Lighthouse still holds its original 1874 lens of which type, named for its French inventor?
Ledger art
Ledger art. The prisoners drew on pages from account books in place of buffalo hide; their jailer, Richard Pratt, went on to found the Carlisle Indian school.
Q 14Which fort north of St. Augustine was, in 1738, the first legally sanctioned free Black settlement in today's US?
Fort Mose
Fort Mose. Spain promised freedom to people escaping slavery in the British colonies if they became Catholic and the men served in its militia, and their town guarded St. Augustine's northern edge.
Q 15Which 1763 agreement handed Florida, and St. Augustine, to Great Britain?
Treaty of Paris
The Treaty of Paris handed Florida to Britain so that Spain could get back Havana, which the British had captured; most of St. Augustine's Spanish residents then sailed for Cuba.
Q 16Three signers of the Declaration of Independence were held by the British at St. Augustine after which city fell in 1780?
Charleston
Charleston. Thomas Heyward Jr., Arthur Middleton and Edward Rutledge, all South Carolina signers, were shipped south after the city surrendered and went free in a prisoner exchange in July 1781.
Q 17Under which agreement, ratified in 1821, did Florida pass from Spain to the United States?
Adams–Onís Treaty
The Adams–Onís Treaty paid Spain nothing for Florida; the United States instead took on about $5 million in outstanding claims connected with its own citizens.
Q 18Which Seminole leader was imprisoned in St. Augustine's fort during the Second Seminole War?
Osceola
Osceola came to talk peace under a white flag in 1837 and was seized instead; held in the fort, he was moved that winter to a South Carolina prison, where he died within weeks.
Q 19The tycoon who rebuilt St. Augustine as a Gilded Age resort made his fortune as a co-founder of which company?
Standard Oil
Standard Oil. Rockefeller's partner wintered in St. Augustine in the 1880s, found it charming but short of good hotels and transport, and set about building both himself.
Q 20Which inventor's company supplied the electric lighting for St. Augustine's Ponce de Leon Hotel in 1888?
Thomas Edison
Thomas Edison's dynamos lit the hotel from opening day, and guests were said to be so wary of the new switches that staff were hired to turn the lights on and off for them.
Fresnel
Fresnel. Rifle shots once broke 19 of the lens's glass prisms, and a local volunteer league raised the money to have it restored.
Q 24What became of St. Augustine's first lighthouse, the earliest in Florida, in 1880?
It collapsed into the sea
It collapsed into the sea. Erosion had been eating at the shore for years, so a taller replacement was built and lit in 1874, six years before the old tower finally fell.
Q 25The Bridge of Lions is named for its marble copies of the Medici lions, which stand in which Italian city?
Florence
Florence. The originals have stood in the Loggia dei Lanzi since 1789, after they were moved from Rome; the bridge opened in 1927, just after the land boom behind it went bust.
Q 26The Bridge of Lions connects downtown St. Augustine to which barrier island?
Anastasia
Anastasia Island is also where the Spanish quarried the stone for the Castillo de San Marcos, ferrying the blocks across the bay that the bridge now spans.
Q 27St. Augustine's Cathedral Basilica holds which record in the contiguous United States?
Oldest Christian congregation
Oldest Christian congregation. The parish dates from the Mass said at the 1565 landing, but its church is far younger: the present building was not finished until 1797.
Q 28A St. Augustine park promoted since 1904 by 'Diamond Lil' McConnell trades on which legend tied to Ponce de León?
The Fountain of Youth
The Fountain of Youth. Ponce de León never mentioned any such spring in his own letters; a Spanish chronicler pinned the story on him in 1535, years after his death.
Q 29Where in St. Augustine was Martin Luther King Jr. arrested in June 1964?
At the Monson Motor Lodge
At the Monson Motor Lodge, on the steps of its whites-only restaurant. A week later its manager poured acid into the pool to drive out a swim-in, and the photographs went around the world.
Q 30St. Augustine dentist Robert Hayling invited which civil rights group, led by Martin Luther King Jr., to the city in 1964?
SCLC
SCLC. Hayling had led the local NAACP youth council, but after Klansmen beat him at a 1963 rally and the NAACP then asked him to resign, he turned to King's organisation.