Creating a historical narrative for a place has traditionally entailed consulting the source materials that have managed to survive over time, interpreting those records, and constructing a narrative for how that place came to be. Until recently historians have often viewed technology and its ability to contribute to this process with skepticism if not outright hostility. Contrary to this view, geographic information systems (GIS) can add to, and not detract from, the creation of a historical narrative for a specific place. Apart from the Great Fire of Seattle in 1889, the regrading and removal of Denny Hill (1898–1930) arguably represents the most iconic period in Seattle’s urban history. The Denny Regrade, the removal of a 245- foot hill that once buttressed Seattle’s downtown retail and commercial districts, remains prominent in the historical consciousness of Seattle, as it represents a period of intense and dramatic change. GIS, and in particular historical GIS, offers the opportunity to more deeply explore and re- create the history of the Denny Regrade due to its inherent ability to spatially integrate, visualize, and analyze information. Using the Denny Regrade as a case study, this article examines the application of historical GIS to a topic in urban history across an extended temporal scale (1893–2008). Three main areas are discussed. The historical context of the Denny Regrade is explored; components of the historical GIS developed for the study are examined; and examples of geovisualizations and new historical data and information are presented.