Town of Hillsboro
The Town of Hillsboro, historically known as “The Gap” or “Hillsboro,” has carved out a distinct, historic niche nestled in the gap of Short Hill Mountain just east of the Blue Ridge Mountains. Serving as a scenic gateway west of Leesburg, it is one of the Commonwealth’s smallest and best-preserved 18th- and 19th-century rural villages, with the entire linear town proudly listed on the National Register of Historic Places. Walking down its main street feels like stepping straight into our region’s rich agrarian past, where historic stone buildings sit tight alongside the old Charles Town Pike (Route 9).
Today, the town has re-engineered itself into a bustling center for local commerce, right-sized businesses, and hyper-local agritourism. It serves as a true regional hub, completely surrounded by magnificent, rolling vine-covered slopes, farm-to-table markets, and craft breweries. About four miles west of Hillsboro, take Harpers Ferry Rd and head north to find some of the best wineries in the region.
If you really want a taste of the area, grab lunch at the Stoneybrook Market enjoy a wood-fired pizza at Market In The Gap, or explore the historic Old Stone School. The grounds of the Old Stone School also serve as the ultimate neighborhood gathering space; this year, the beloved Music in the Gap summer concert series is officially scheduled to return!
These free community concerts will run on Friday evenings from July 10 through September 11, 2026. Held outdoors at the Gap Stage, most performances kick off around 7:00 PM and feature a rotating, stellar lineup of regional roots, rock, blues, and folk artists. For an outdoor excursion before the music starts, Key’s Gap is just minutes away, providing easy access to the mountain ridges of the Appalachian Trail. Supporting a lifestyle so deeply connected to regional heritage, live music, and open space is just a normal, wonderful part of living in Western Loudoun County.
Curious about homes available in Hillsboro?
Explore available homes in and around Hillsboro ↗ with Diana Geremia Real Estate.
Want to get a little lost instead?
It’s no Google Maps, but getting lost out west is half the fun.
Know a great spot? 📌 Drop your own pin!
