The paper outline three basic categories of urban phenomenology based upon the simple notion of a trajectory thorough a network of streets. This formal notion gives rise to three different phases of such a trajectory—where the movement stops, when it proceeds unproblematically, and when several possibilities for choosing the further trajectory present themselves; thus, the locale, the street, and the square, as indicated in the title. Based on the Peircean notions of First-, Second-, and Thirdness, the paper makes a first investigation as to which aspects of urban experience are connected to these three categories.