Highland County is a county located in the Commonwealth of Virginia. As of the 2010, the population was estimated to be 2,321. Its county seat is Monterey. Known as "Virginia's Little Switzerland", Highland County is the least populous county in Virginia. Highland lays claim to being one of the least populous counties and one of the highest average elevations east of the Mississippi River.
Settlement of this portion of the Colony of Virginia by Europeans began around 1745. Located west of the Tidewater and Piedmont regions in Virginia and also west of the Shenandoah Valley, this area is beyond (known in old Virginia as the "Transmountaine") the Blue Ridge Mountains. Rather than cross such a formidable physical barrier, most early settlers came southerly up the Valley across the Potomac River from Maryland and Pennsylvania. Many followed the Great Wagon Road, also known as the Valley Pike (U.S. Route 11 in modern times). As German immigrants began to push over the mountains to the northern area of the present county, those of Scots-Irish descent settled in the southern part.
Even after Virginia and the other 12 colonies won their independence from Great Britain after the American Revolutionary War, the area remained sparsely populated. In the 1840s, the historic Staunton-Parkersburg Turnpike was built through the area. Engineered by Claudius Crozet through the mountainous terrain, it was a toll road partially funded by the Virginia Board of Public Works. The turnpike formed an important link between the upper Shenandoah Valley with the Ohio River.
Control of the Staunton-Parkersburg Turnpike became crucial during the American Civil War (1861–1865). By all accounts, documented in many letters home from young troops, a miserable winter in 1861 was spent by Union and Confederate troops holding opposing high elevation positions along the road. The Battle of McDowell, the first Confederate victory of Stonewall Jackson's Shenandoah Valley campaign, took place at McDowell on May 8, 1862.
In the 20th century, the Turnpike was re-designated as U.S. Route 250. In the 21st century, it remains Highland County's major east-west roadway, and crossing into West Virginia, becomes a National Scenic Byway.