Though it doesn’t get nearly the history textbook attention as cities like Boston, New York, and DC, Charlottesville is one of our nation’s oldest cities, and played an important role in early United States and Virginia history. Sitting on a trade route called the Three Notch’d Road, it was formed by charter in 1762. Much of downtown Charlottesville has been built around centuries-old buildings, and just to the outskirts of town, you’ll find Thomas Jefferson’s home, Monticello, Ash Lawn-Highland (home of James Monroe), James Madison’s Montpelier, and plenty more colonial and early American landmarks. All of these historic homesteads are open to the public, and every Charlottesville tourist must visit Monticello at the very least. Thomas Jefferson is, after all, the father of this fair city.