Welcome to “The Gap”

Come for the history, stay for a while.

The Town of Hillsboro, just 50 miles outside of Washington, D.C., is one of the Commonwealth’s best preserved historic assets and is hub to a robust agricultural and recreation region in northwest Loudoun County.

The Hillsboro Gap is a water gap in the Short Hill Mountain formed by the North Fork of the Catoctin Creek. In colonial times the Vestal Gap Road running through the gap and the Town of Hillsboro was the main artery between Alexandria and Winchester. That road eventually became the Charles Town Pike and today’s modern day Route 9.

Today Hillsboro is surrounded by wineries, craft breweries, farm-to-table dining, local artisan shops and outdoor recreation activities including the Appalachian Trail. Many area venues offer sweeping views of the Blue Ridge Mountains and the rolling countryside, lush and green in the summer and golden with hay and corn husk tops in the fall.

TRAILS AND TOURS

View from the Bear's Den Overlook along the Appalachian Trail accessed just west of Hillsboro.

Gateway to the Blueridge

Hillsboro is located 6 miles east of Keyes Gap, a wind gap in the Blue Ridge Mountain which is on the border of Loudoun County, Virginia and Jefferson County, West Virginia. The gap is traversed by Virginia State Route 9.

The Keyes Gap trail head provides hikers with easy access to the Appalachian Trail.

Traveling north along the trail it's a 13.6 mile out-and-back to Historic Harpers Ferry. Generally considered a moderately challenging route, the round-trip takes about 6 hours to complete. Popular with backpackers, hikers and campers. Dog friendly.

Traveling south, the trail follows the Blue Ridge Mountain ridge to the Bear's Den Overlook and Trail Center near Bluemont where distance hikers can find short-term resupply, showers, laundry services and bunk rooms.

For more information about hiking opportunities along the Appalachian Trail near Hillsboro, visit nps.gov/appa.