Despite a well-established literature on the sociology of sex work and sociology of sex and place, currently we know very little about how and why sex workers choose to work on the streets that they do. Using the case study of a city in upstate New York and drawing upon Michel de Certeau’s (1984) theory of spatial patterns, this study builds on these literatures by discussing the importance of place and space in relation to sex work, namely how and why sex workers choose their locations for business. Data are drawn from semistructured interviews with female and male sex workers, police officers, and an outreach worker. The findings reveal the ways in which these spaces of street sex work are reworked by sex workers in response to strategies imposed by the police, community residents, and others. Within these spaces, sex workers employ a number of tactics to maximize business and minimize detection, arrest, and violence from clients and other sex workers. Directions for future research are also discussed.