The district's commercial area is along Washington and Madison Streets.

Middleburg was established in 1787, but the historic district includes a few 18th-century structures, with most dating to the mid-19th century.

The district includes the Red Fox Inn & Tavern, the oldest building in town and listed individually on the National Register of Historic Places.

Little development took place in Middleburg in the late 19th century, and the district includes no examples of Victorian architecture.

This article about a property in Loudoun County, Virginia on the National Register of Historic Places is a stub.