Template:On this day/May 21
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- 1791 – Thomas Jefferson and James Madison embarked on a month-long journey to New England and upstate New York, the object of which was not politics, as Hamiltonians and later historians assumed, but, in Madison's words, "health, recreation and curiosity."
- 1822 – Mosby Monroe Parsons, US officer in the Mexican–American War and brigadier general of the Confederate States Army, born in Charlottesville (d. 1865).
- 1924 – The Robert E. Lee Statue in Lee Park was unveiled. The population of Charlottesville temporarily swelled by more than 25,000 that week as members of Grand Camp Confederate Veterans, Department of Virginia, Virginia State Division, Sons of Confederate Veterans and the Virginia Division of the United Confederate Veterans converged on the city, not only for the ceremony but for their annual state reunions.