The concept of historical conservation and character definition is reflected in the Liverpool Street of Elmina and Kingsway Street of Cape Coast in Ghana. The features of these streets are changing owing to urbanization and to the development of commercial retail. In this study, we investigated the character-defining features of Kingsway Street and Liverpool Street within an 800 m radius relative to the Cape Coast and Elmina Castles, respectively, which are known for their landmark roles as historical artifacts. We adopted a combination of mapping, philology, and fractal geometry to assess the character-defining features of each street. The key changes in the features of the two streets and the similarities between these features are emphasized in our results. The features of both streets have undergone rapid changes in terms of economic retail activities, which represent the central element defining the characters of theses treets. Furthermore, the 18th and 19th century architecture along these streets is gradually losing their original features because of undocumented and unguided renovations, as well as retrofitting works that are based on the discretion and taste of building owners.