Small-towns around the turn of the twentieth century served as social, economic, and entertainment centers for the surrounding rural population and their Main Streets were the face of rural America. Although small-town Main Streets are a part of the larger urban system, they have often been neglected in academic scholarship on urban places. This dissertation utilizes several commonplace data sources for Main Street businesses to reveal and analyze connectivity patterns for several small-town communities in upstate New York from the 1880s through the first decade of the twentieth century. Rather than regarding small-town communities as merely being ‘linked’ in one direction as part of a metropolitan hinterland, evidence illustrates that each of these places also had their own webs of connectivities with many regional and distant places. These webs of connectivity helped shape the networks of commerce and sociability that often define small-town America. Hotel registers, store invoice records, local newspaper columns outlining travel into and out of local communities, and invoice data each offer very detailed individual-centered information that have remarkable spatial and temporal attributes. In addition to these place-based sources route books for traveling salesmen, circuses, and other entertainment troupes also reveal how places are connected through circuits of exchange at all levels of the urban system. Through the use of historical GIS and visualization analysis, the data illuminate a fish-eye lens model for everyday movements of people and products at the turn of the twentieth century.