This paper explores the geocoding methods used on historical city directory addresses for the purposes of studying and visualizing 100 years of urban development, business growth, as well as streetscape changes for a small city in Ontario, Canada. Using historical city directories, alongside maps and fire insurance plans, the researchers studied cardinal changes, street name changes and address number shifts for the years 1900-2000 to create a seamless open-access discoverable and interactive map. Users can look up a century’s worth of business information for endless research opportunities, as well as study families and their movements throughout the decades.