Charlottesville Trivia
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96 free Charlottesville trivia questions with answers — geography quiz, new questions added Oct 2026.
48 free Charlottesville trivia questions with answers. Charlottesville is a small city with an outsized history: two presidents, a university that is a World Heritage Site, a nickel-famous house on a hill, and the bar where the Dave Matthews Band got its start. This quiz covers the founding in 1762 and Jack Jouett's ride, Monticello and the University of Virginia, the Downtown Mall and the Corner, the Cavaliers' 2019 title, the destruction of Vinegar Hill and the events of 2017. It is written for locals, UVA students and alumni, and visitors who want to know the place beyond the guidebook. About a third of the questions are easy, a third are pub-quiz medium and the rest will stump anyone who has not lived here. Every answer is verified against the city's and university's reference pages. Use it for a Charlottesville trivia night, a road-trip warm-up, or bragging rights on the Downtown Mall.
30 of 96 questions with answers and explanations. Play the quiz
Q 01Which two US presidents lived in Charlottesville?
Thomas Jefferson and James Monroe
Thomas Jefferson and James Monroe were neighbors on purpose: Jefferson urged his friend to buy the farm beside Monticello in 1793. James Madison's Montpelier lies in neighboring Orange County.
Q 02Charlottesville honors Queen Charlotte, the wife of which British king?
George III
George III had married Charlotte of Mecklenburg-Strelitz in 1761, and the new Albemarle County seat, established the following year, was named for the new queen.
Q 03What is Charlottesville's common nickname?
C'ville
C'ville is how locals shorten Charlottesville, and the city's alternative weekly took the nickname for its own title, which it styles C-VILLE Weekly.
Q 04What is Charlottesville's Downtown Mall?
A car-free Main Street
A car-free Main Street, not a shopping center: the city closed East Main Street to traffic to revive its fading downtown, and the brick-paved mall opened in 1976.
Q 05Around 1784, Thomas Jefferson carried out one of America's earliest archaeological digs on what near Charlottesville?
A Native burial mound
A Native burial mound drew Jefferson after Indian visitors were seen paying respects there; he cut a trench through it and published what he found in Notes on the State of Virginia.
Q 06Who rode 40 miles in June 1781 to warn Jefferson at Monticello of a British raid?
Jack Jouett
Jack Jouett spotted Banastre Tarleton's cavalry near Louisa and outrode them overnight to Monticello. Jefferson and most legislators escaped, and Jouett became the Paul Revere of the South.
Q 07Which Union general's 1864 raid on Charlottesville was turned back at Rio Hill?
George Armstrong Custer
George Armstrong Custer surprised a Confederate horse-artillery camp at Rio Hill and was driven off. He came back with Sheridan in March 1865, and the town surrendered to them.
Q 08Which downtown African American neighborhood did the city raze in 1965 as urban renewal?
Vinegar Hill
Vinegar Hill was the city's Black business hub; voters chose to raze it by just 36 votes, in a referendum held while a poll tax kept many Black residents from the polls.
Q 09Which architect designed Old Cabell Hall at the south end of UVA's Lawn?
Stanford White
Stanford White of McKim, Mead & White designed Old Cabell Hall after the Rotunda fire of 1895, closing off the south end of the Lawn that Jefferson had left open to the mountains.
Q 10What did Jefferson put at the head of UVA's Lawn instead of a chapel?
Library
A library filled the Rotunda at the head of the Lawn, and Jefferson left a chapel out of his plan altogether; the university added one only late in the nineteenth century.
Q 11Jefferson modeled the University of Virginia's Rotunda on which ancient building?
The Pantheon in Rome
The Pantheon in Rome was Jefferson's model, built at a much smaller scale. A fire that began in the annex in 1895 gutted the Rotunda, which had to be rebuilt.
Q 12Which poet enrolled at the University of Virginia in 1826, the year Jefferson died?
Edgar Allan Poe
Edgar Allan Poe spent February to December 1826 at the university, excelling in Latin and French before gambling debts ended his stay; the Raven Society preserves his room, 13 West Range.
Q 13Jefferson's epitaph names the Declaration, his university and what else?
A religious freedom law
Q 21Charlottesville-raised Boyd Tinsley played which instrument in a hometown rock band until 2018?
Violin
Violin came to the band for one song only: in 1991 Tinsley, who led his own group, was asked to guest on a single demo track, and by 1992 he had joined full time.
Q 22Which comedy writer and actress earned a drama degree from the University of Virginia in 1992?
Tina Fey
Tina Fey studied playwriting and acting in Charlottesville, graduated in 1992 and left for Chicago's Second City; by 1997 she was writing for Saturday Night Live.
Q 23Which small area a few blocks from the Downtown Mall is the original center of Charlottesville?
Court Square
A religious freedom law, Virginia's 1786 statute, made the stone. Jefferson asked for three achievements and 'not a word more', so his two terms as president went unmentioned.
Q 14The name Monticello comes from Italian words meaning what?
Little mountain
Little mountain is what monticello means in Italian, a diminutive of monte, and it fits: Jefferson built the house on the leveled summit of a small peak outside town.
Q 15Monticello appeared on the reverse of which US coin every year from 1938 to 2003?
The nickel
The Jefferson nickel carried Monticello on its reverse from 1938 through 2003; the 2004-05 Westward Journey designs interrupted the run before Monticello returned in 2006.
Q 16Which Italian Renaissance architect's principles did Jefferson follow in designing Monticello?
Andrea Palladio
Andrea Palladio's Four Books of Architecture shaped Jefferson's eye: Monticello's portico and symmetry follow the Italian's rules, and the same pages guided his designs for the University of Virginia.
Q 17Which organization bought Monticello from the Levy family in 1923?
The Thomas Jefferson Foundation
The Thomas Jefferson Memorial Foundation, now the Thomas Jefferson Foundation, paid Jefferson Monroe Levy $500,000 for Monticello in 1923 after the Levy family had preserved the house since 1834.
Q 18James Monroe's estate near Monticello, long called Ash Lawn, was renamed what in 2016?
Highland
Highland was Monroe's own name for the farm. A later owner rebranded it Ash Lawn, and the College of William & Mary, his alma mater and the estate's owner, restored the original in 2016.
Q 19Which famous rock group formed in Charlottesville in 1991?
Dave Matthews Band
Dave Matthews Band formed in Charlottesville in 1991, when bartender Dave Matthews, urged by lawyer friend Ross Hoffman, recorded demos and recruited local jazz players.
Q 20Jefferson struggled for decades at Monticello to make which product, now a specialty of the countryside around Charlottesville?
Wine
Wine defeated Jefferson: he replanted his Monticello vineyards again and again, in an age when rot and pests doomed European vines. The surrounding hills became the Monticello wine appellation in 1984.
Court Square's courthouse doubled as the town's church: with no church building in early Charlottesville, congregations held services in the courtroom, and Jefferson sometimes attended.
Q 24What is the name of the commercial strip of bars and eateries along University Avenue next to UVA?
The Corner
The Corner began as a literal corner, a few businesses at the entrance to the university's grounds, and the name spread to the blocks of shops and bars that grew up around it.
Q 25Charlottesville lies along which river, a tributary of the James?
Rivanna
Rivanna is the river on the city's eastern edge; it meets the James at Columbia. The Jeffersons owned land along it, and a young Thomas Jefferson pushed to have it cleared for boats.
Q 26Charlottesville is closest to which of these cities?
Richmond
Richmond, the state capital, lies about 70 miles southeast, near enough that Virginia's government fled from there to Charlottesville when British troops advanced in 1781.
Q 27Which two major highways pass through Charlottesville?
Interstate 64 and US Route 29
Interstate 64 and US Route 29 cross here, though I-64 nearly missed the city: Virginia chose a southern route through Lynchburg in 1959, and federal officials overruled it in 1961.
Q 28Which Amtrak long-distance train links Charlottesville with Chicago and New York City?
The Cardinal
The Cardinal nearly vanished: Amtrak cancelled it in September 1981, and a congressional mandate put it back on the rails the following January, three days a week.
Q 29Which scientific institution has its headquarters in Charlottesville?
National Radio Astronomy Observatory
National Radio Astronomy Observatory headquarters sit on Edgemont Road beside the university, a long way from its telescopes, which include the Very Large Array in New Mexico.
Q 30UVA's men's basketball team, the 2019 national champion, plays under which nickname?
The Cavaliers
The Cavaliers beat Texas Tech 85-77 in overtime for the 2019 title, a year after becoming the first men's No. 1 seed ever to lose to a 16 seed, UMBC.