When studying and investigating the history of a property or neighbourhood, common resources often sought by researchers include air photos, fire insurance plans and historical maps. These will provide information about what an area looked like, often offering the building’s footprint and surrounding landscape. Timespan studies will no doubt show growth, development and possibly changes to the buildings of interest. But what the rich resources don’ttell the researcher is information about the people connected to those buildings. Who lived or worked there? What did they do for a living? Did they move often? Did they change jobs regularly? These types of questions can’t be answered with just maps alone as they require a detailed census to go along with it. To fill this type of need, Geospatial Centre staff at the University of Waterloo Library embarked on a massive-scale digitization and geo-location city directory project –one that had started in 2019, has involved at least 40 staff members, and still has a couple years to go before completion. This paper will summarize the project thus far, with a focus on the journey of geocoding historical streets.