Middleburg

Attractive boutiques and restaurants line U.S. 50, the main street of this charming country town. Now a hub of Loudoun County's wine and horse culture, this region is rich with history. 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). Today, many of Middleburg's homes include horse farms, and the town is known for its steeplechases and fox hunts in spring and fall. It's a good base for exploring the area's booming wine scene, though roads out to the vineyards are often unpaved and narrow.