This article aims to assess how historical thinking, as defined in the research literature and practiced in schools, can be accessed by analyzing physical spaces. Since the 1990s, "historical thinking" has typically been associated with doing the work that historians do, meaning analyzing documents, weighing evidence, and making arguments. More recently, these inquiry-based approaches to learning history have been extended to physical spaces such as museums and historic sites. This study proposes expanding the concept of historical thinking by using urban landscapes as sites of inquiry. To explore this idea, five historians and ten beginning college students took part in "historical walks" around neighborhoods in New York City and Philadelphia, using their observations to draw conclusions and interpret the histories of the places they visited. In this undertaking, these individuals emulated the now largely forgotten figure of the "walking historian," who collected evidence not in archives, but in three-dimensional spaces.