The area around here was surveyed by George Washington in 1763, when it was known as Chinn's Crossroads. It was considered strategic because of its location midway on the Winchester-Alexandria route (roughly what is now U.S. 50). Loudoun County also had the largest militia in the state of Virginia during the Revolutionary War. Many of Middleburg's homes include horse farms, and the town is known for its steeplechases and fox hunts in spring and fall. Attractive boutiques and stores line U.S. 50 (the main street). Roads out to the vineyards are often unpaved and narrow.