Template:On this day/April 20
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- 1861 – Civil War: That evening the Scottsville Guard, a militia unit commanded by Captain Henry Gantt, received a telegram ordering them to arms. Their immediate assignment was to board a Charlottesville train destined to capture the weapons and storage arsenal in Harpers Ferry.
- 1902 – Monticello lost a long-time resident when Willis Sheldon, who has been gatekeeper for nearly a half century, died on Jefferson’s mountain. He “was buried this afternoon at 3 o’clock in the colored burying grounds near the Jefferson mansion,” the Daily Progress reported the day after he died. “The deceased had been blind for years, and was always found at the post until a few days ago he became too feeble for duty."
- 1991 – With violinist Boyd Tinsley of the Boyd Tinsley Band as a guest, the newly formed Dave Matthews Band played their first public performance at Charlottesville's Earth Day Festival.
- 2006 – The Free Speech Monument is dedicated on the Downtown Mall.
- 2019 – City of Charlottesville officially opens McIntire Park pedestrian bridge and McIntire Skate Park.
- 2020 – The Downtown Grille announced it is closing up after more than 20 years in business on Charlottesville's Downtown Mall.