- Settling of the Loudoun area began between 1725 and 1730, while it was still owned by Lord Fairfax. Permanent settlers came from Pennsylvania, New Jersey and Maryland. During the same period, settlers from eastern Virginia of English Cavalier stock came to lower Loudoun and established large tobacco plantations.
- During the War of 1812, Loudoun County served briefly as a temporary refuge for the President and important state papers. The Constitution and other state papers were brought to Rokeby, near Leesburg, for safekeeping when the British burned Washington. President Madison established headquarters at Belmont, where he was the guest of Ludwell Lee.
- During the Civil War, Colonel John Mosby and his Rangers were active in Loudoun County, which was also the home of the Laurel Brigade, a famous Confederate Cavalry unit commanded by Elijah V. White of Leesburg. A national cemetery near Leesburg marks the site of the Battle of Balls Bluff, where Oliver Wendell Holmes Jr., then a young Union soldier, fought in 1861.
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