Hillsboro, VA

Hillsboro is a town in western Loudoun County, Virginia, set inside Hillsboro Gap where the North Fork of Catoctin Creek cuts through Short Hill Mountain. The 2020 census counted 114 residents. Virginia Route 9 passes through the town, following an older east-west route between the Potomac Valley and Winchester. The gap gives Hillsboro a compact setting: the road, creek, mountain slopes, and historic buildings all sit close together. The stream stays close to the road.

The town was established in 1752 and was first known simply as The Gap. Colonial travelers used Vestal’s Gap Road through this opening, a route later known as Charles Town Pike and now carried by Route 9. Hillsboro’s entire town is listed on the National Register of Historic Places, and its linear village form still follows the old road. The place is small, but its geography tells the town’s story: a crossing through Short Hill that became a village, a highway, and one of Loudoun County’s preserved historic settings.