Winfield's Main Street between 8th and 11th has held on to its late-nineteenth-century character better than most Kansas county seats. The Cowley County National Bank Building, the Winfield National Bank Building, and the Pettit Cleaners Building are all on the National Register and visible from a single corner.
The Cowley County Courthouse just east of Main, a 1962 modernist rebuild, sits where the original limestone courthouse stood through most of the town's history. Wander a few blocks east into the leafy residential streets for the W. H. Coffin House and the W. P. Hackney House, both grand late-Victorian homes in the Queen Anne style.