Background: Insufficient physical activity is a significant concern because a growing body of research demonstrates that physical activity during adolescence has numerous benefits on physical health, mental health, and educational achievement. A less-studied area of physical activity research is how physical activity participation in adolescence relates to educational and career aspirations and attainment. Methods: Using the Add Health dataset consisting of over 15,000 participants, this study addressed several research questions relating to the long-term benefits of habitual physical activity in adolescence. Physical activity levels in adolescence and associations with activity participation in later adolescence and young adulthood were explored as were relationships with physical activity participation in adolescence and educational ambition and attainment in young adulthood. Moderator variables including adolescent sex, race, and age were also examined. Results: Results indicated several significant relationships between physical activity in adolescence and future physical activity and educational attainment outcomes. Conclusions: Given short- and long-term benefits of physical activity, school personnel and parents should ensure children are meeting the required activity guidelines for children and find ways to keep children active as they approach adolescence.