Hillsboro, VA

Tucked into a scenic mountain pass in western Loudoun County, Hillsboro is one of Virginia's smallest and most distinctive historic towns. With a population of barely over a hundred residents, the entire community lines a single picturesque stretch of Route 9, nestled between the slopes of Short Hill Mountain and the waters of Catoctin Creek. Beautiful stone cottages and historic brick homes sit right along the roadway, creating an intimate atmosphere where the surrounding landscape is part of everyday life.

ATTRFamartin / CC BY-SA 4.0

Settled in the mid-1700s as a colonial travel route, Hillsboro is officially recognized on the National Register of Historic Places from end to end. Today, the Old Stone School serves as the town's social anchor, hosting community concerts, seasonal festivals, and weekend markets throughout the year. For newcomers considering a move to Northern Virginia wine country, Hillsboro offers quiet country living and mountain views while keeping you close to shopping and dining in nearby Purcellville and Leesburg.