Highland County Historic Homes

There are currently no historic homes for sale in Highland County...sorry!

Highland County History

Settlement of the area that came to be known as Highland County, Virginia, started around 1745 when the Germans began to push over the mountains to the northern area of the present county and the Scotch-Irish began to find land in the southern part. The county's remote location was noted by the settlers who were petitioning for their land before the Revolution. Asking for 50,000 acres on the "head branches of the James River", they said, "the lands are very remote and lying among great mountains, being about 200 miles from any landing."

The county is comprised of five major valleys, and ten streams flow out of Highland to form the headwaters of the James and Potomac Rivers. At Hightown, northwest of the county seat of Monterey, a barn was built in such a way that all the rain that runs off the roof on one side drains into the Potomac Basin and off the other side into the James River. The farm is appropriately named "Dividing Waters Farm."

The Indians called the Cowpasture River the "Wallawhatoola," meaning "the river that bends." Legend says the three "pasture" rivers were named by hunters who killed a buffalo calf at the first stream (the Calfpasture River), a cow at the second (the Cowpasture River), and a bull at the third stream (the Bullpasture River).

The first reported road in the area was a 32-mile bridle path to a mill in 1751. When the county was created in 1847, the county seat was described as "a patch of woods and laurel thickets on the saddle between the two straight creeks." The only building was the John Cook house and tavern. Once the hunting ground of a small band of Shawnee warriors, Highland began to open to development when the Staunton-Parkersburg Turnpike was constructed in 1838 under the supervision of Claudius Crozet. By the time of the Civil War, Highland was able to enlist more than 500 men as soldiers, most of whom served in the Confederate Army.