Middleburg is history, picturesque countryside and lots of charm. Middleburg, Virginia was established in 1787 by American Revolutionary War Lieutenant Colonel and Virginia statesman John Leven Powell, who purchased the property from Joseph Chinn, a cousin of George Washington. Powell changed the name from “Chinn’s Crossroads” to Middleburg because the town was the halfway point between Alexandria and Winchester along the popular Ashby Gap trading route, along what is today Rte. 50.
The town has a rich history, including serving as the site of two skirmishes in 1863 as part of the Gettysburg Campaign during the Civil War. After the turn of the century, the town became a popular destination for foxhunting and steeplechasing, earning it a reputation as the “Nation’s Horse and Hunt Capital”.