Charlottesville was the home of two Presidents, Thomas Jefferson and James Monroe. During their terms as Governor of Virginia, they lived in Charlottesville, and traveled to and from Richmond, along the 71-mile (114 km) historic Three Notch'd Road. Orange, located 26 miles (42 km) northeast of the city, was the hometown of President James Madison. The University of Virginia, founded by Jefferson and one of the original Public Ivies, straddles the city's southwestern border. Monticello, 3 miles (4.8 km) southeast of the city, is, along with the University of Virginia, a UNESCO World Heritage Site, attracting thousands of tourists every year.
At the time of European encounter, part of the area that became Charlottesville was occupied by a Monacan village called Monasukapanough.
An Act of the Assembly of Albemarle County established Charlottesville in 1762. Thomas Walker was named its first trustee. It was situated along a trade route called Three Notched Road (present day U.S. Route 250), which led from Richmond to the Great Valley. The town took its name from Charlotte of Mecklenburg-Strelitz, who became queen consort of Great Britain when she married King George III in 1761.
During the American Revolutionary War, Congress imprisoned the Convention Army in Charlottesville at the Albemarle Barracks between 1779 and 1781. The Governor and legislators had to temporarily abandon the capitol and on June 4, 1781, Jack Jouett warned the Virginia Legislature meeting at Monticello of an intended raid by Colonel Banastre Tarleton, allowing a narrow escape.
Unlike much of Virginia, Charlottesville was spared the brunt of the American Civil War. The only battle to take place in Charlottesville was the skirmish at Rio Hill, an encounter in which George Armstrong Custer briefly engaged local Confederate Home Guards before retreating. The mayor surrendered the city to Custer's men to keep the town from being burned. The Charlottesville Factory, founded c. 1820–30, was accidentally burnt during General Sheridan's 1865 raid through the Shenandoah Valley. The factory had been taken over by the Confederacy and used to manufacture woolen clothing for the soldiers. It caught fire when some coals taken by Union troops to burn the nearby railroad bridge dropped on the floor. The factory was rebuilt immediately and was known as the Woolen Mills until its liquidation in 1962.