Shepherdstown is a town in Jefferson County, West Virginia, United States, located in the lower Shenandoah Valley along the Potomac River. Home to Shepherd University, the town's population was 1,734 at the time of the 2010 census.

Martinsburg is a city in and the county seat of Berkeley County, West Virginia, United States, in the tip of the state's Eastern Panhandle region in the lower Shenandoah Valley. Its population was 17,454 in the 2019 census estimate, making it the largest city in the Eastern Panhandle and the eighth-largest municipality in the state. Martinsburg is part of the Hagerstown-Martinsburg, MD-WV Metropolitan Statistical Area.

Winchester is an independent city located in the northern portion of the Commonwealth of Virginia, United States. It is the county seat of Frederick County, although the two are separate jurisdictions. The Bureau of Economic Analysis combines the city of Winchester with surrounding Frederick County for statistical purposes. As of the 2010 census, the city's population was 26,203. As of 2019, its population is an estimated 28,078.Winchester is the principal city of the Winchester, Virginia–West Virginia, metropolitan statistical area, which is a part of the Baltimore–Washington metropolitan area. Winchester is home to Shenandoah University and the Museum of the Shenandoah Valley.

Loudoun County () is located in the northern part of the Commonwealth of Virginia in the United States. In 2019, the population was estimated at 413,538, making it Virginia's third-most populous county. Loudoun County's seat is Leesburg. Loudoun County is part of the Washington–Arlington–Alexandria, DC–VA–MD–WV Metropolitan Statistical Area. As of 2018, Loudoun County had a median household income of $136,268. Since 2008, the county has been ranked first in the U.S. in median household income among jurisdictions with a population of 65,000 or more.