The town was established in 1787 by American Revolutionary War Lieutenant Colonel and Virginia statesman, Leven Powell. He purchased the land for Middleburg at $2.50 per acre in 1763 from Joseph Chinn, a first cousin of George Washington. It had been called Chinn's Crossroads, and was then called Powell Town. When Leven Powell declined to have the town named after him, the town was called Middleburgh, and later, simply Middleburg. The village is located midway between the port of Alexandria and Winchester, Virginia, on the Ashby Gap trading route (now followed by U.S. Route 50).