Research in urban geography tends to focus on large cities. This dissertation recognizes that cities come in many sizes; it argues that it is important to study small towns as urban places. Further, it finds that urban processes occurring in small towns are not just useful to expand our understanding of these places, but as indicators of broader urban change, challenges, and futures. This dissertation asks how and why small towns are changing. It expands the base of literature on small towns through research into American cultural understandings of these places, as well as a statistical analysis of 3,000 small cities. To contextualize urban change, I examine seven small towns, considering how the local landscape is changing, using interviews, archival documents, news media, and municipal representations. I find that the traditional small town of the American imagination no longer exists. Nostalgia is not enough to protect small towns from urban forces of contemporary change. Small towns are becoming less compact, more diverse, and more connected to outside influences. These changes affect the form, the "hard city," and the character, the "soft city," of small towns in the United States. Yet despite these changes, nostalgia persists, putting changes in urban form in conflict with the perceived city.