Re-cartography is a designerly mapping practice that aims to challenge dominant spatial epistemologies while expanding the scope of our spatial imagination. Particularly relevant to contemporary complex spatial problematics, and emerging within the context of urbanism, re-cartography is an intrinsically projective practice that is orientated towards a (re)shaping of the environment. This paper presents a short processual account of three re-cartographies of southwest Flanders. These three cases represent an ongoing attempt to reimagine the region in contemporary terms. Taken together, they remap the area in terms of multiplicity, heterogeneity, and hybridity, and reimagine the territory as a dynamic layering of different historical processes and relationships. To this end, the maps rethink common cartographic strategies and procedures—such as element selection, categorization, and symbolization, periodization, layering, scaling, and atlas composition—and recombine them in novel ways. They also demonstrate the relevance of re-cartography as an urban design tool: as a practice with the capacity to incorporate various perspectives, both context and potential, re-cartography is able to suggest a universe of latent possiblities within a given site. Of interest to cartographic theory is the observation that re-cartography treats both the territory and the map as ongoing processes. In this sense, the cases reflect the almost pragmatic coexistence of two seemingly contradictory cartographic ontologies at the heart of urbanism: the consideration of the map as a (partial) workable mirror and a concomitant engagement with the postrepresentational quality of the map as a project.