Urbanization in Alabama has been driven and influenced by a number of factors over the course of the state’s history. Examined from a geographic standpoint, the sizes and spatial distributions of Alabama’s cities have been chiefly driven at different times by access to the state’s navigable waterways; proximity to its major cotton-cultivating regions; access to significant railroad infrastructure; proximity to the state’s major coal and iron ore deposits; access to significant highway infrastructure; proximity to various “institutional industries” (defined here as the combination of county seats of government, public universities, permanent military installations, and the site of the state capital); and the process of suburbanization. This study employs qualitative data-collection and quantitative analysis methods to determine the possibility of modeling the explanatory power of these variables relative to the populations of the state’s twenty largest cities in each decade since 1820 in a manner that complements and aligns with the prior literature on the subject using multiple linear regression. The resulting models are able to successfully capture a single statistically-significant geographic variable with great accuracy, although the results are also somewhat more mixed when examining possible secondary and tertiary predictors of city population. The research serves as a stepping stone towards developing a statistical means of analyzing and understanding the impacts of various geographic factors on urban population that is both adaptable to other regions of the world and is able to produce outputs that are relatively easy to map and visualize.