Abstract Our objective is to explore the adequacy of traditional structural explanations for the often-documented association between size of place and urbanity traits and to raise the possibility that cultural factors, too often neglected in urban sociology, play an important role in this relationship. Using survey data from a sample ages 15–89, we compare four sets of respondents with different child/adult residential configurations: those who grew up in nonurban places and as adults live in nonurban places (locals), those who grew up in nonurban places but as adults reside in urban places (cosmopolitans), those who grew up in urban places and reside in urban places as adults (urbanites), and those reared in urban places but residing as adults in nonurban places (escapees). The sets are compared with respect to six different measures of urbanity—anonymity, tolerance, alienation, community social bonds, deviant behavior, and involvement in unconventional subcultures. Our results support the contention that size has an independent effect on urbanity, but various structural theories generally fail to explain many aspects of the relationship. Instead, the views of Hummon (1990) about a shared culture of place are most consistent with our findings. We conclude by noting the kinds of contributions such a culturalist perspective can make to understanding the link between size of place and individual characteristics.