This study focuses on the transition from horse-powered to automotive transit in Washington, DC and explores how the city’s cultural landscape was adapted to fit this new means of transportation. Three main sources are used to establish an inventory of horse- and automotive-related structures: Sanborn Fire Insurance Maps, Baist’s Real Estate Atlas of Surveys, and Boyd’s City Directories of the District of Columbia. Inventoried structures are documented in their form and function between 1888 and 1935 to further understand the transitional period between transportation methods and changes to the city’s infrastructure and livelihood. Documented changes are analyzed further in the context of the increasing prominence of the automobile in the 20th century. Trends in car manufacturing, specifically the Ford company, are included to support trends found in the analysis. Additionally, an inventory of extant structures is conducted to better understand the fate of these structures and their contemporary uses, if any.