Through two studies, this project tested the idea that it is the convergence of individual differences and social environmental factors across extended periods of time that are pivotal in influencing how active a person is at any given time and the long-term health-related outcomes associated with different activity patterns. The first study developed archival data refined from the Terman Life Cycle study, which followed 1,528 individuals from childhood in 1922 through death. Growth curve analyses, hierarchical linear regression, and survival analyses were used to investigate patterns of physical activity across adulthood, from average age 25 to age 61, to examine individual psychosocial differences, and to determine how different trajectories relate to health, well-being, and longevity across the lifespan. There was a general pattern of decelerating decline in activity with age, but substantial individual variation that could partly be explained by child and adult psychosocial variables. Childhood energy and sociability, adult extraversion and neuroticism for males, and adult self-rated health and mental adjustment for females were strong predictors of levels and changes in physical activity. Active individuals were more likely to be healthy at midlife and old age, even after controlling for baseline health. Importantly, maintaining or increasing activity related to better health in older age, and lower mortality risk. The second study used a cross-sectional assessment to determine personality characteristics that theoretically and empirically distinguish different activity patterns (active, sedentary, or variable), and to examine links among personality, physical activity, and health. A more active personality strongly correlated with better self-rated health and well-being, fewer perceived barriers and more perceived benefits to being active, and better social relationships. In both studies, personality impacted both physical activity levels and health, and physical activity consistently related to better health outcomes, including higher self-rated health, subjective well-being, and increased levels of energy. All together, the studies suggest that health outcomes relate to physical activity trajectories, but this may depend on the fit between the person and subsequent experiences.