Middletown is known for the Wayside Theater, a professional theater company established in 1961. It is housed in a two-story, brick, former movie theater that was built on the site of the late-nineteenth-century Shenandoah Normal School, which burned in the early 1940s. Adjacent, at 7843 Main, is the former Middletown State Bank (c. 1915), a brick, one-story, three-bay building that retains most of its character-defining features including corbeled brickwork, central double-leaf entrance doors, and a recessed brick frieze panel.
The two-story, gable-roofed, three-bay weatherboarded log building (c. 1800) at 7846 Main was the house of Jacob Danner. At the turn of the nineteenth century, Danner, along with Anthony Kline, were known for their production of fine clocks, watches, and surveying equipment. The single-story porch and the bracketed cornice were added in a later nineteenth-century remodeling.