50 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 50 questions with answers and explanations. Play the quiz
Q 01Charlottesville is named after which British queen?
Charlotte of Mecklenburg-Strelitz
The town was established by an act of the Albemarle County assembly in 1762, when Charlotte was the new bride of George III.
Q 02Which two US presidents lived in Charlottesville?
Thomas Jefferson and James Monroe
Both commuted to Richmond as governors along the 71-mile Three Notch'd Road; Madison's home, Montpelier, is in nearby Orange.
Q 03What was Charlottesville's population at the 2020 census?
About 46,500
Combined with Albemarle County for statistics, the area comes to roughly 160,000 people.
Q 04What is Charlottesville's common nickname?
C'ville
The University of Virginia gives the city an unusually young median age of under 30.
Q 05In what year was Charlottesville established by an act of the Albemarle County assembly?
1762
It sat on the Three Notched Road, a trade route from Richmond to the Great Valley that is now US Route 250.
Q 06Who was named Charlottesville's first trustee at its founding?
Thomas Walker
Walker was a physician and explorer who is credited with the first recorded crossing of the Cumberland Gap.
Q 07Which Monacan village occupied part of the Charlottesville area before European settlement?
Monasukapanough
The Monacans were pushed off their land and dispersed as far as North Carolina, Tennessee and possibly Canada.
Q 08Who 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 09Which 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 10Which downtown African American neighborhood did the city raze in 1965 as urban renewal?
Vinegar Hill
One hundred thirty homes, five Black-owned businesses and a church were destroyed; the land sat undeveloped until the late 1970s.
Q 11Which architect designed Old Cabell Hall at the south end of UVA's Lawn?
Stanford White
Jefferson designed the Rotunda at the other end; the dormitory rooms along the Lawn are reserved for distinguished students.
Q 12In what year did Thomas Jefferson found the University of Virginia?
1819
Jefferson had lost faith in his own alma mater, William & Mary, partly because it required students to recite a catechism.
Q 13Jefferson 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 21Which famous rock group formed in Charlottesville in 1991?
Dave Matthews Band
Dave Matthews was tending bar downtown when a lawyer friend talked him into recording a demo of his songs.
Q 22At which Charlottesville bar was Dave Matthews working when he started the band?
Miller's
Local jazz drummer Carter Beauford and saxophonist LeRoi Moore were his first recruits.
Q 23Which instrument did founding DMB member Boyd Tinsley play?
Violin
Stefan Lessard joined on bass while still a junior in high school, recommended by UVA jazz director John D'earth.
Q 14Which poet enrolled at the University of Virginia in 1826, the year Jefferson died?
Edgar Allan Poe
He excelled in Latin during his single semester; the Raven Society still maintains his room, 13 West Range.
Q 15In what year did Monticello and the University of Virginia become a UNESCO World Heritage Site?
1987
They are the only such site in the US designed by a former president.
Q 16The name Monticello comes from Italian words meaning what?
Little mountain
The house sits on an 850-foot peak in the Southwest Mountains, about three miles southeast of downtown.
Q 17Monticello appeared on the reverse of which US coin every year from 1938 to 2003?
The nickel
Jefferson's portrait is on the front, making it a two-sided tribute to the same man; the Westward Journey designs interrupted Monticello in 2004-05 before it returned in 2006.
Q 18Which Italian Renaissance architect's principles did Jefferson follow in designing Monticello?
Andrea Palladio
The most dramatic element is the octagonal dome, whose room was rarely used because it was hot in summer, cold in winter and hard to reach.
Q 19Which organization bought Monticello in 1923 and still operates it as a house museum?
The Thomas Jefferson Foundation
Jefferson Monroe Levy sold it for $500,000 after his family had owned and preserved the house for decades.
Q 20James Monroe's estate near Monticello, long called Ash Lawn, was renamed what in 2016?
Highland
Operated since Monroe's death by his alma mater, the College of William & Mary, the estate dropped 'Ash Lawn' from its name in 2016.
Q 24Charlottesville's Downtown Mall is notable as one of the nation's longest what?
Outdoor pedestrian malls
It is home to the Paramount Theater, the Virginia Discovery Museum and the 3,500-seat Ting Pavilion.
Q 25Charlottesville'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 26Which small area a few blocks from the Downtown Mall is the original center of Charlottesville?
Court Square
Several of its buildings date back to the city's founding in 1762.
Q 27What is the name of the commercial strip of bars and eateries along University Avenue next to UVA?
The Corner
Much of the university's Greek life sits on nearby Rugby Road.
Q 28Charlottesville lies along which river, a tributary of the James?
Rivanna
The city sits on rolling hills between the university to its west and the river to its east.
Q 29Roughly how far is Charlottesville from Washington, D.C.?
About 100 miles
Richmond is closer, at about 72 miles away.
Q 30Which two major highways pass through Charlottesville?
Interstate 64 and US Route 29
I-64 runs east to Richmond and west to Staunton, where it meets I-81.