Extending along State Route 9, Hillsboro is a well-preserved example of the typical 19th-century linear community and rural mill town of Northern Virginia. The village grew along a minor trade artery connecting Leesburg in Loudoun County 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 Hillsboro Historic District boundary was increased to incorporate buildings and structures that more fully represent the history and development of the incorporated Loudoun County Town of Hillsboro. The primary resources in the Hillsboro Historic District reflect mid-18th- to mid-19th-century development of the town, preserved in part due to its relative isolation and partially due to the influence of the Quaker tradition of its early residents.
[VLR Listed: 9/17/2009; NRHP Listed: 3/23/2010]