Social trends show that contemporary fathers are spending increased time with their children and that active play and outdoor recreation are important features of their relationships. Dominant ideals of masculinity can differ by settings, which in turn guide men’s understandings and practices of fathering regarding the functions of and opportunities afforded by active play. This article draws on individual interview data from a study of fathers residing in three Canadian settings—large urban, small urban, and rural—to elucidate father masculinities and highlight similarities and differences in how men describe connections between fathering and active play with their children. Findings suggest that for large urban, small urban, and rural fathers, respectively, play functions as a means of emotional engagement, development of capacity for outdoor activities, and teaching children survival skills. We propose that the sociostructural and cultural dynamics of place shape masculine identities and influence men’s understandings of fathering.