Extending along State Route 9, Hillsboro is a well-preserved example of the typical 19th-century linear community of Northern Virginia. The village grew along a minor trade artery connecting Leesburg with Charles Town (now West Virginia) during the early 19th century. Its residents provided economic and social services to farmers of the vicinity, and the town retains its rural setting, being surrounded by the scenically beautiful countryside for which western Loudoun County is noted. The architectural fabric of the Hillsboro Historic District consists mainly of two-story, gable-roofed stone residences, illustrating the influence of Pennsylvania vernacular building types on Northern Virginia. Victorian porch and bay window additions indicate that residents remained current with architectural fashions.

In 2009, the district boundary was increased to incorporate buildings and structures that more fully represent the history and development of the village of Hillsboro.
[VLR Listed: 9/17/2009; NRHP Listed: 3/23/2010]