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46 free Charlottesville trivia questions with answers — geography quiz, new questions added Aug 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 46 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 lived two miles apart outside Charlottesville, Jefferson at Monticello and Monroe at the farm later called Ash Lawn; Madison's home was in Orange County.
Q 02What was Charlottesville's population at the 2020 census?
About 46,500
The 2020 census counted 46,553 people in Charlottesville, about 46,500; with surrounding Albemarle County the local population is roughly 160,000.
Q 03What is Charlottesville's common nickname?
C'ville
Locals shorten Charlottesville to C'ville, the name carried by the city's alt-weekly newspaper C-VILLE Weekly and used across University of Virginia student life.
Q 04In what year did Virginia's General Assembly establish the town of Charlottesville?
1762
The General Assembly chartered Charlottesville in 1762 on the Three Notched Road, the colonial trade route from Richmond toward the Shenandoah Valley that US Route 250 now follows.
Q 05Which Monacan village occupied part of the Charlottesville area before European settlement?
Monasukapanough
Monasukapanough, a Monacan village on John Smith's 1612 map, stood on a riverbank just north of today's Charlottesville; Jefferson excavated its burial mound in the 1780s.
Q 06Who rode 40 miles in June 1781 to warn Jefferson at Monticello of a British raid?
Jack Jouett
Colonel Banastre Tarleton's cavalry arrived to find the legislators gone; Jouett is remembered as the "Paul Revere of the South".
Q 07Which Union general skirmished with Home Guards at Rio Hill, Charlottesville's only Civil War battle?
George Armstrong Custer
A year later the mayor surrendered the town to Custer and Sheridan to keep it from being burned.
Q 08Which downtown African American neighborhood did the city raze in 1965 as urban renewal?
Vinegar Hill
Vinegar Hill, the Black business district along West Main Street, was razed in 1965 under a federal urban-renewal program, displacing about 600 residents; much of the land sat empty into the 1980s.
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, completed in 1898, closing the south end of the Lawn that Jefferson had left open toward the mountains.
Q 10In what year did Thomas Jefferson found the University of Virginia?
1819
The Virginia General Assembly chartered the University of Virginia on January 25, 1819; Jefferson designed its grounds and classes began in March 1825, a year before his death.
Q 11Jefferson modeled the University of Virginia's Rotunda on which ancient building?
The Pantheon in Rome
Its dome is 77 feet across, exactly half the Pantheon's, and the building was gutted by fire in 1895 before being 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 13In what year did Monticello and the University of Virginia become a UNESCO World Heritage Site?
1987
Q 21Which instrument did founding DMB member Boyd Tinsley play?
Violin
Boyd Tinsley, a Charlottesville-raised violinist, first guested on the band's 'Tripping Billies' and then joined full time, playing violin with DMB until 2018.
Q 22Charlottesville's Downtown Mall amphitheater took which company's name in 2019?
Ting
Ting became the venue's third telecom naming sponsor in 2019, following nTelos and Sprint.
Q 23Which small area a few blocks from the Downtown Mall is the original center of Charlottesville?
Court Square
Court Square, the original town center laid out around the Albemarle County Courthouse, keeps several early-19th-century buildings; the courthouse's oldest section dates from 1803.
UNESCO inscribed Monticello and the University of Virginia together in 1987, the only World Heritage Site in the United States designed by a US president.
Q 14The name Monticello comes from Italian words meaning what?
Little mountain
Monticello is Italian for 'little mountain', from monte plus the diminutive -cello; Jefferson's house sits on an 850-foot summit about three miles southeast of downtown Charlottesville.
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
Jefferson called Andrea Palladio's Four Books of Architecture his 'bible'; Monticello's portico, symmetry and dome follow Palladian principles, though the octagonal dome room was rarely used.
Q 17Which organization bought Monticello from Jefferson Monroe Levy 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
Monroe himself named the farm Highland; later owners called it Ash Lawn, and the College of William & Mary, which received the estate in 1974, restored the name Highland 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 20At which Charlottesville bar was Dave Matthews working when he started the band?
Miller's
Matthews tended bar at Miller's, a Downtown Mall jazz spot where drummer Carter Beauford and saxophonist LeRoi Moore played; they became his first recruits in 1991.
Q 24What is the name of the commercial strip of bars and eateries along University Avenue next to UVA?
The Corner
The Corner is the strip of bars, restaurants and shops along University Avenue facing the UVA Grounds, with the White Spot diner among its long-time fixtures.
Q 25Charlottesville lies along which river, a tributary of the James?
Rivanna
The Rivanna River flows along Charlottesville's eastern edge and joins the James at Columbia in Fluvanna County; the city lies between the university on the west and the river on the east.
Q 26Roughly how far is Charlottesville from Washington, D.C.?
About 100 miles
Charlottesville sits about 100 miles southwest of Washington, D.C., roughly two hours by car; Richmond is closer at about 70 miles to the southeast.
Q 27Which two major highways pass through Charlottesville?
Interstate 64 and US Route 29
Interstate 64 runs east to Richmond and west to Staunton, where it meets I-81, while US Route 29 carries traffic north toward Washington and south toward Lynchburg.
Q 28Which Amtrak long-distance train links Charlottesville with Chicago and New York City?
The Cardinal
The Cardinal runs three days a week between New York and Chicago via Washington, Charlottesville and the New River Gorge; the Crescent to New Orleans also stops at the West Main Street station.
Q 29Which scientific institution has its headquarters in Charlottesville?
National Radio Astronomy Observatory
The National Radio Astronomy Observatory moved its headquarters from Green Bank, West Virginia, to Charlottesville in 1965; it sits on Edgemont Road beside the UVA Grounds.
Q 30Which UVA team won the 2019 NCAA men's basketball championship?
The Cavaliers
The Virginia Cavaliers beat Texas Tech 85-77 in overtime for the 2019 title, a year after becoming the first No. 1 seed to lose to a 16 seed, UMBC.