Middleway, a historic village located at the intersection of ancient Native American trails, has a rich history rooted in its strategic location and natural resources. Initially attracting settlers like John Smith in 1729 due to its water source at Turkey Run, Middleway quickly developed into a milling and farming community by the Revolutionary War era. Chartered as Smithfield in 1798, the town's name changed to Middleway in 1807 with the establishment of a post office to avoid confusion with another Virginia town. Middleway thrived in the early 1800s as a regional trading hub but suffered a decline when the Baltimore and Ohio Railroad bypassed it in favor of Summit Point. This decline, however, helped preserve its 19th-century architectural charm. The Civil War brought turmoil, with Middleway at one point serving as a hospital site and experiencing the "Battle of Smithfield" in 1864. Post-war hardships saw many residents leave, but the town maintained its historic character. In the mid-20th century, a manufacturing plant reinvigorated the area, and in 1980, the Middleway Historic District was recognized and added to the National Register of Historic Places. Today, the Middleway Conservancy works to preserve the village's historical significance and charm.