Known as Virginia's “Little Switzerland” because of its mountainous terrain, remote Highland County has the state's smallest population. The county is divided by parallel mountain ranges that form five well-defined valleys: from east to west, these are the Cowpasture, Bullpasture, Monterey, Bluegrass, and Allegheny valleys. Much of the county's spectacular scenic landscape varies from forested mountain slopes to grassy rolling hills dotted with grazing sheep and cattle. From around 1745, English, German, and Scots-Irish settlers came to the area. Although the county has always been remote because of its mountainous geography, communication improved with the construction in 1838 of the Staunton-Parkersburg Turnpike (much of it now U.S. 250). The turnpike also created an avenue of commerce between the Shenandoah Valley and the Ohio River and led to the establishment of businesses serving travelers' needs.
The county was formed in March 1847 from parts of neighboring counties and by 1848 a courthouse and jail (HI1) were built at Monterey, the county seat. With the exception of the strategically important Battle of McDowell on May 8, 1862, which was fought near the village of McDowell, the county did not experience much fighting or devastation. Modest log buildings were typical in the early years of settlement, but by the mid-nineteenth century, brick construction became common. Since the mid-twentieth century, few changes have altered Highland County's rural landscapes and village streets, but the county increasingly attracts new residents, most of whom are retirees drawn to its tranquility. Livestock farming, forestry, and the maple sugar industry remain the economic mainstay. For a few days in early March, Highland County's annual Maple Festival attracts more visitors than the county's year-round population.
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