How many cities are there in Delaware? There are a total of 57 towns and cities in the state of Delaware. Top 10 biggest cities by population are Wilmington, Dover, Newark, Middletown, Smyrna, Milford, Seaford, Georgetown, Elsmere, and New Castle while top ten largest cities by land area are Dover, Wilmington, Middletown, Milford, Newark, Smyrna, Seaford, Georgetown, Lewes, and Bridgeville.