This chapter looks at the intertwined evolution of two different ideas throughout the past century: that of ‘territory’, that has been reshaped and redefined in the field of architecture and urbanism, and that of ‘digital’, that while becoming dominant, has been influencing territorial studies. While territory emerged as a subject, as the largescale object where to observe urbanization and landscape, the question of its representation becomes key in understanding its interaction with another emerging field, that of ‘digital’. It is thus through the representation of territory that this chapter conjugates digital and territorial turn. More in particular, we observe cartographies as and made by architects and urbanist, that we define transformative: with this notion, we intend cartography oriented not only to represent, but also to transform of the same object of representation, that is to say the territory itself. The digital evolution of transformative cartographies builds up from two parallel paths, that of an emerging physical territorial dimension and that of emerging technologies. Paths that converge and diverge over the decades: after a crossing turn between 8’0s and 90s, a forking path seems to rather distinguish the most recent experiences.