The period of significance for the district is 1861 to 1965 when most of the buildings were constructed. Unlike many historic downtowns in Iowa, Winterset replaced its initial frame buildings with masonry buildings because of economic prosperity, and not because of fires.[2] In addition to Piquenard, other architects of note who contributed buildings in the district include William Foster (Crawford/Jefferson Block, 1873; Schwaner/Centennial Block, 1876), L.W. Foster (Madisonian Building, 1872; City Hall Block/Jones & Tidrick, 1875), Joseph S. Blake (Firemen's Hall/City Hall/Light Plant, 1888, 1889, 1923), Frank E. Wetherell (Bevington Building/Masonic Temple, 1914 remodel), and Louis A. Simon (U.S. Post Office, 1935).