Highland County is a county located in the Commonwealth of Virginia. As of the 2020 census, the population was 2,232, making it the state's least populous county. Its county seat is Monterey. Known as "Virginia's Switzerland" or "Virginia's Little Switzerland", Highland County is the least populous jurisdiction in Virginia, including counties and independent cities. Highland lays claim to being one of the least populous counties and one of the highest average elevations east of the Mississippi River.

The Shenandoah Valley is a geographic valley and cultural region of western Virginia and the Eastern Panhandle of West Virginia in the United States. The Valley is bounded to the east by the Blue Ridge Mountains, to the west by the eastern front of the Ridge-and-Valley Appalachians, to the north by the Potomac River, to the south by the James River, and to the Southwest by the New River Valley. The cultural region covers a larger area that includes all of the Valley plus the Virginia Highlands to the west and the Roanoke Valley to the south. It is physiographically located within the Ridge and Valley Province and is a portion of the Great Appalachian Valley.