How many cities are there in Kentucky? There are a total of 782 towns and cities in the state of Kentucky. Top 10 biggest cities by population are Louisville, Lexington, Bowling Green, Owensboro, Covington, Hopkinsville, Richmond, Florence, Georgetown, and Henderson while top ten largest cities by land area are Morehead, Princeton, Coal Run Village, Erlanger, Shelbyville, Burnside, Winchester, Corbin, Eddyville, and Jenkins.