Highland lays claim to being one of the least populous counties and one of the highest average elevations east of the Mississippi River.

Rather than cross such a formidable physical barrier, most early settlers came southerly up the Valley across the Potomac River from Maryland and Pennsylvania.

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.

Engineered by Claudius Crozet through the mountainous terrain, it was a toll road partially funded by the Virginia Board of Public Works.

In the 21st century, it remains Highland County's major east–west roadway, and crossing into West Virginia, becomes a National Scenic Byway.

[7] The county's western border is naturally defined and lies along the Eastern Continental Divide in the Allegheny Mountains.

The northern and southern boundaries of the county are defined more artificially, cutting across numerous mountain ridges and valleys.

West of Monterey, the divide is roughly centered along the path of U.S. Route 250; however, in eastern Highland County, the James watershed extends further northward.

The Jackson River flows out of Bluegrass Valley to the east through Vanderpool Gap approximately 4 miles (6.4 km) south of Hightown.

[33][34] The tornado's classification on the Fujita scale is reported by the National Weather Service in its database to be unknown,[33] though another document records it as an F1.

A barn and chicken house were damaged during this storm and a building was lifted off its foundation in the Big Valley area.

[32] Since 1955, Highland County has experienced twenty instances of severe hail, which is defined by the National Weather Service as hailstones having a diameter of at least 1 inch (2.5 cm).

If the old definition of at least 3⁄4 inch (1.9 cm) diameter hailstones is considered, the county has experienced twenty-two instances of severe hail during the same period.

Cattle grazing is especially suited for the area as the mountainous terrain leaves only a small fraction of the total land suitable for cultivation.

Wool production is a significant industry in the county,[42] which was ranked fifth in Virginia in 2010 for the largest number of lamb and sheep with approximately 4,500 head.

[51] All primary routes and over 213 miles (343 km) of secondary roads in the county are serviced and maintained by the Virginia Department of Transportation.

[52] Upon entering the county, U.S. 250 descends into the Back Creek valley, whereafter it crosses the long ridge of Lantz mountain.

[52] Approximately 3⁄4 mile (1.2 km) after entering the county, U.S. 220 crosses the South Branch Potomac River at Forks of Waters.

Leaving Forks of Waters, U.S. 220 continues in a southwesterly direction on a roughly straight and level route passing the village of Possum Trot to the town of Monterey.

[10][55] South of Monterey, U.S. 220 passes by Trimble Knob, a conical shaped hill that was an active volcano or diatreme 35 million years ago.

Approximately 15 miles (24 km) south of Monterey, U.S. 220 enters Bath County, Virginia near the village of Bolar.

[49] Commercial air transportation is available at the Shenandoah Valley Regional Airport in neighboring Augusta County, Virginia.

[62][63] The prospects of a railroad reaching Highland were limited due to the mountainous terrain and a general lack of sufficient traffic to make such an investment economically viable.

[68][69] The first record of educational services in the area of Highland County is from 1755 with the arrival of a teacher by the name of William Steuart.

[76] This designation is applied because of Highland's remote characteristics with a low population density and limited access to healthcare and other services.

[91] The local government of Highland County consists of a three-member Board of Supervisors who are elected at-large to serve four-year terms.

[109][110] The mountains of Highland have historically attracted many tourists to the region, including Henry Ford, Thomas Edison, Harvey Firestone, and other prominent inventors and businessmen who visited the area in 1918.

[115] The festival attracts over 60,000 people annually to the county during the event and has been designated a Local Legacy by the Library of Congress.

[115][116] Highland also hosts a seasonal farmers' market,[117] and the Allegheny Mountain School, an organization to help secure community food systems.