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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.
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Q 01St. Augustine, Florida, was founded by settlers from which country?
Spain
Founded in 1565, it is the oldest continuously inhabited European settlement in the contiguous United States.
Q 02Which Spanish admiral founded St. Augustine on September 8, 1565?
Pedro Menéndez de Avilés
He was Florida's first governor and had been sent partly to wipe out the French Huguenots at Fort Caroline.
Q 03Why was the settlement named San Agustín?
Land was first sighted on the feast day of St. Augustine
The fleet spotted the Florida coast on August 28, eleven days before the formal landing.
Q 04Which continuously inhabited city in a US territory is older than St. Augustine?
San Juan, Puerto Rico
San Juan dates to 1521; Jamestown was not founded until 1607.
Q 05Which Native people lived in the area, in the village of Seloy, when the Spanish arrived?
Timucua
The Franciscan Mission Nombre de Dios was founded at the landing point to serve their villages.
Q 06What does 'Matanzas', the name of the inlet and river south of the city, mean in Spanish?
Slaughters
Menéndez executed the shipwrecked French Huguenots of Jean Ribault there in 1565.
Q 07Which English privateer sacked and burned St. Augustine in 1586?
Sir Francis Drake
The town's first parish church burned in the raid; the killing of his sergeant major prompted Drake to raze the town.
Q 08The Castillo de San Marcos is built from what local stone?
Coquina
The name means 'small shells'; it was quarried on Anastasia Island and ferried across the bay.
Q 09Why did British cannon fire have so little effect on the Castillo's walls?
The soft shell stone absorbed the cannonballs
Rather than shattering, the balls simply sank into the coquina.
Q 10In what year was construction of the Castillo completed, after 23 years of work?
1695
Work had begun in October 1672; the fort was never taken by force under any of its four flags.
Q 11How many times has the Castillo been taken by force in its history?
Never
It changed hands five times between Spain, Britain and the United States, always peacefully.
Q 12Under American rule the Castillo was renamed after which Revolutionary War figure?
Francis Marion
Fort Marion later held a famous Seminole leader and, decades on, Geronimo's Chiricahua Apache.
Q 13Which Native American art form is said to have originated among Plains prisoners held at the fort?
Ledger art
Howling Wolf of the southern Cheyenne was among the artists imprisoned there.
Q 21The Ponce de Leon Hotel was the first major project of which famous architecture firm?
Carrère & Hastings
They went on to design the New York Public Library; the hotel was the first of its kind built entirely of poured concrete.
Q 22Since 1968 the old Ponce de Leon Hotel has been the centrepiece of which institution?
Flagler College
The rival Hotel Alcazar across the street now houses the Lightner Museum.
Q 23How tall is the black-and-white spiral-striped St. Augustine Lighthouse tower, completed in 1874?
165 feet
It stands at the north end of the island and still houses its original first-order Fresnel lens.
Q 14Fort Mose, founded north of the city in 1738, holds what distinction?
First legally sanctioned free Black settlement in what is now the US
Escaped slaves from the Carolinas were granted freedom in exchange for militia service and conversion to Catholicism.
Q 15Which 1763 agreement handed Florida, and St. Augustine, to Great Britain?
Treaty of Paris
Spain got Havana and Manila back in the deal; Florida returned to Spain twenty years later.
Q 16Which of these Founding Fathers was NOT among the three held prisoner in the Castillo by the British?
Charles Carroll
All three captives had signed the Declaration for South Carolina and were seized when Charleston fell.
Q 17Under which agreement, ratified in 1821, did Florida pass from Spain to the United States?
Adams–Onís Treaty
St. Augustine and Pensacola then alternated as capital of the Florida Territory.
Q 18Which Seminole leader was imprisoned in the fort during the Second Seminole War?
Osceola
Twenty other Seminole prisoners squeezed out through an embrasure and escaped in 1837.
Q 19Which Standard Oil co-founder transformed St. Augustine into a Gilded Age resort in the 1880s?
Henry Flagler
He found the town charming but its hotels and transport inadequate, and set about fixing both.
Q 20Which friend of Flagler's supplied the electricity system for the Ponce de Leon Hotel?
Thomas Edison
It was among the first buildings in the world designed for electric light from the start, with Tiffany glass in the dining room.
Q 24In which year was Florida's first lighthouse lit at St. Augustine?
1824
During the Civil War a local customs officer led a 'Coastal Guard' that disabled lighthouses to help blockade runners.
Q 25The Bridge of Lions takes its name from marble copies of lions found in which Italian city?
Florence
They are Carrara-marble copies of the Medici lions in the Loggia dei Lanzi; the bascule bridge opened in 1927.
Q 26The Bridge of Lions connects downtown St. Augustine to which barrier island?
Anastasia
It replaced a wooden span known simply as the Bridge to Anastasia Island.
Q 27What record does the parish of the Cathedral Basilica of St. Augustine, dating to 1565, hold?
Oldest Christian congregation in the contiguous US
The current church was built from 1793 to 1797 after the first burned in Drake's 1586 raid; it became a basilica in 1976.
Q 28Which explorer is the Fountain of Youth Archaeological Park loosely linked to?
Juan Ponce de León
The park's 'spring' was promoted from 1904 by Luella 'Diamond Lil' McConnell, who invented tales to amuse tourists.
Q 29Where in St. Augustine was Martin Luther King Jr. arrested in June 1964?
On the steps of the Monson Motor Lodge restaurant
Images from the St. Augustine campaign helped push the Civil Rights Act of 1964 through the Senate.
Q 30Which local dentist and civil rights leader invited the SCLC and King to St. Augustine?
Robert Hayling
He had founded an NAACP Youth Council that staged wade-ins at segregated pools.