History

Travelers on the Ashby’s Gap road were stopping here from the 1730s, and the spot was long known as Chinn’s Crossroads. In 1787 Revolutionary War officer Leven Powell, who had bought the land from Joseph Chinn, a cousin of George Washington, established a town here. Declining to name it for himself, he called it Middleburg because it lay midway between Alexandria and Winchester on the route that is now U.S. Route 50.

The town became a coach stop on the turnpike and, by the mid-1800s, the trading center for lower Loudoun and upper Fauquier. During the Civil War Union troops occupied it in 1862, cavalry clashed in and around town during the June 1863 Gettysburg campaign, and Mosby’s Rangers were known to gather at the Red Fox Inn. The war left the town poorer and smaller.

After 1900, foxhunting and steeplechasing brought new life, and Middleburg built a reputation as a capital of horse and hunt country. Its tree-lined streets and brick sidewalks preserve buildings from the late 1700s to the early 1900s, and the town center has been a historic district on the state and national registers since 1981–82.