In this paper, I explore how doing digital mapping work helped me rethink my traditional scholarly work through a conversation between the digital and the material. I begin with a description of a process involving finding racetracks converted into housing developments and move on to a discussion of the mapping of information broadly defined. I looked for references to horse racing, searched maps for their presence, and then went to the modern-day map and satellite image to see if their presence remained. What emerged from my work is the seemingly universal presence of racetracks in almost every location. While I continue to map racetracks in my project on New York City horse racing, a more process-oriented idea of mapping also emerged, a type of mental mapping of how and where racing existed and how one might begin to contextualize these maps, both geographic and mental.