Today, as a result of fast-paced societal transformations, many small towns face severe developmental challenges and an uncertain future. Departing from the broader theory of developmental disequilibrium, we launch the concept of urban hibernation to explain the process of periodic small-town regress. The concept—along with its key stages and turning points—is presented to the background of urbanization processes encountered in Poland. At the same time, the focus on small towns offers an alternative and more context-sensitive explication to eclectic development models inherent to larger cities. As such, we argue that the concept of urban hibernation is apt to serve as a more precise research and planning tool in the context of small towns, and particularly in the critical moments of rise and recession. By applying a historical perspective, we address the importance of proper identification of the various and ever-changing city-forming factors, including their role for spatial planning at different scales. Urban hibernation should thus be considered as an intrinsic part of the geographic environment, which, due to the volatility of its socio-economic components, transcends the traditional rural–urban divide. Our conceptual contribution may thus serve as a background for a fuller understanding of the variability and dynamics of intra-urban structures.