The Downtown Commercial District of Winchester, Kentucky, contains one of the more remarkable collections of late nineteenth century commercial architecture in existence in Kentucky. The district contains an almost continuous band of Victorian era commercial architecture broken only by the Clark County Courthouse. Contained within the district is a high concentration of distinctive landmark buildings which are notable for their local adherence to high architectural styles and use of materials and surface textures. Downtown architecture is an accurate reflection of the community's changing sense of aesthetic. Buildings such as the Brown-Proctor Hotel, the Elks Building, the Clark County National Bank, the Citizens National Bank, the Clark County Courthouse, the Odd Fellows Building, Leeds Theatre, and others are elegant expressions of local as well as national architectural design during period of economic growth.
In addition, the terraced "high side" of Main Street is an unusual response to the demands of commercial block development and the natural environment. In all areas of the district there is a relative lack of alterations to both the original storefronts and upper facades of these buildings.
Periodic changes in architectural and commercial aesthetics during the twentieth century are in little evidence on Main Street because change has come slowly and deliberately to Winchester. This thoroughly unique and heavily concentrated collection of commercial architecture reflects nearly one hundred fifty years of economic and cultural development that makes the Winchester Main Street Commercial District outstanding among the core areas of Kentucky's cities.
Additional importance of the district can be found in the integral role it played in the economic and cultural development of the mountain region of eastern Kentucky. Downtown Winchester served as the distribution center for raw materials, such as timber, iron and coal that followed the railroad lines down the mountains to be funneled out to the nation at large through Winchester. The fortunes created in natural resources in the Appalachian region helped to build the banks, hotels, shops and homes in Winchester. The development of the eastern mountains of the state is, in part, reflected in the physical appearances of the Winchester Downtown Commercial District.