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The first European settler in what is now Ritchie County was John Bunnell, who built a cabin near Pennsboro by 1800. Before 1810, John Webster bought Bunnell's land and built the Old Stone House.
Daniel Haymond was one of the first people to settle in northeastern Ritchie County, in 1817, near the North Fork of the Hughes River. In the 1800s, Virginia's roads helped the area grow. In the late 1830s, the Northwestern Virginia Turnpike was built through the county, connecting Winchester to Parkersburg. By 1850, the county's population had doubled, and it nearly doubled again by 1860. A few years later, the Staunton-Parkersburg Turnpike (now State Route 47) was built through the southern part of the county.
