Hillsboro was established in 1752 in the gap of the Short Hill just east of the Blue Ridge Mountains. Known simply as “The Gap” for its first half century, Hillsboro today stands among the best-preserved 18th/19th-century rural villages in Virginia, with the entire Town on the National Register of Historic Places. Minutes from the Appalachian Trail, Shenandoah River, Harpers Ferry and 11 miles northwest of the Loudoun County seat of Leesburg, historic Hillsboro is the hub of one of Virginia’s largest wine regions and tourism destinations.
