The Fredericktown Courthouse Square Historic District includes a Lancaster Plan courthouse square. In the center of the square is the 2.5-story Second Renaissance Revival style Madison County Courthouse, which was constructed in 1900. The courthouse square plan includes two main streets that extend perpendicular to the central square/courthouse. The downtown district’s streets hold one, two, and three-story brick commercial buildings constructed from the late 19th century through the early-to-mid 1940s. One building located northeast of the courthouse square was constructed circa 1845; this is a limestone building used as a livery/stable. This property is the oldest extant building in the district.