Middlebrook, in the countryside south of Staunton along historic Middlebrook Road, is one of the oldest villages in the region. William and Nancy Scott sold the first 27 lots there in April 1799 to Scots-Irish and German settlers. In 1851, the stagecoach road through the village became the Middlebrook and Brownsburg Turnpike. By the late 19th century, Middlebrook was the center of a prosperous agricultural community and, with 274 inhabitants including an African American community, the county’s largest village. Because 20th-century railroads and highways bypassed Middlebrook, the rows of closely spaced dwellings and stores lining the main road retain the picturesque character of the village’s heyday in the 1880s.