The authors attempt to re-imagine classification systems as emergent systems—where names, categories and associated data structures arise from the bottom up through collective usage. Each has employed cartographic methodology as an interaction metaphor in the design of dynamic, evolving systems that allow participants to create and archive their own itineraries and maps on-line. These systems explore the aesthetic dimensions of the database. The authors have presented and tested prototypes of two developing systems, Subtract the Sky and A Map Larger Than the Territory, in a workshop/exhibition. This article provides a brief description of the premise and implementation of both projects. It concludes with some preliminary findings from the workshop/exhibition and the authors' shared research.