Comparing mobility patterns of adolescents across generations requires methods that incorporate the historicity of human activity. This study examines how adolescent use of space; in terms of leisure time and mobility patterns; has changed across generations in relation to diverse geographic and socioeconomic histories. The data collected from Nashville families includes interviews; parent oral histories; free recall maps; and teen mobility tracks gathered using a wearable Global Positioning System (GPS) device. This paper describes how changes in artifacts; and different levels of community embeddedness have shaped the ways in which todayâ€™s adolescents experience and create spaces outside of school; in comparison to their parentsâ€™ generation. I analyze how daily activity schedules reflect a division of labor in families between parents and their adolescent children; the variety and place-based structure of community learning opportunities in which adolescents participate during their leisure time (with and without parental oversight); the mutually accountable practices through which teens produce and regulate these spaces; and recurring use of cultural materials and artifacts for producing and engaging with these spaces. Observing geography; class; gender; and age constantly working in confluence in the construction of space through time; this paper further challenges the idea that children from urban working-class families experience â€śdeficitsâ€ť while participating in and making practices outside of school. While extant models of activity systems (e.g.; Engestrom et al.; 1999) provide considerable guidance in making sense of adolescents space-time mobility and use of community spaces in leisure time activities; there are dynamic; imaginative components of these spatial practices (de Certeau; 1984) that are not well captured by concepts of rules or divisions of labor within the already-existing community. Finally; this paper reports on a comparison of adolescent and parent/guardian (as recalled; in a map construction task) space-time mobility; where both are treated as a linked collection of activity systems. If culturally relevant pedagogy is important for educating students and challenging institutional inequities in the future (Ladson-Billings; 1995); then we must also know what defines youth culture and learning outside of school in the present.