A simple-sounding challenge - running every street in a city - has a surprisingly complex definition. What counts as a street? What defines a city? OpenStreetMap’s data reflects the world’s messiness, from paths to freeways and boundary schemes for many different definitions of place. This talk explores how StreetFerret interpreted OSM data for pedestrian challenges, covering key tagging practices, boundary selection, and edge cases that challenge our understanding of how the world is organized.