Middletown was chartered on May 4, 1796, by Peter Senseney, a German-born physician who came to this area from Pennsylvania. Although he resided in Winchester, he owned a large tract of land in this area that included a small community known as Senseney Town. Because of its location along the Valley Pike, midway between Stephens City and Strasburg, the name was eventually changed to Middletown. In 1810, Charles Varle in Topographical Description of the Counties of Frederick, Berkeley, and Jefferson Situated in the State of Virginia described Middletown as “situated on the road to Staunton, and in a fine and fertile county, partly limestone land; it contains about 50 houses and 150 souls. Here several taverns and stores are kept.” The Valley Pike runs comfortably through the center of town. Fortunately, the town charter required all houses to be set well back from the road, so when the pike was widened in the 1930s, none of them had to be demolished or moved back to accommodate the new width. The earliest buildings date to the late eighteenth century and are primarily of log construction. During the Civil War, the town was the scene of considerable military activity with troops moving back and forth along the Valley Pike. South of Middletown at 8437 Valley Pike is Cedar Creek Battlefield and Visitors Center.
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