Generativity involves care and concern for future generations as a legacy of the self. It is a central developmental task in midlife for both individual well-being, and for a functioning society. As such, opportunities to foster generativity in youth have lasting benefits. There is growing evidence examining correlates of generativity with youth. To date, however, these studies rely mostly on university samples, and are somewhat homogeneous with respect to demographic representation. At the same time, youth engagement supported by adults has also been linked to youth identity development (generally considered a precursor to generativity) and has been identified as a positive feature in youth programs. While youth engagement likely benefits generative development, there is no empirical research to date linking them together. Therefore, in this chapter we present survey findings from over 600 youth of diverse backgrounds, from a community sample, aged 12 to 28 years old, who participated in various youth programs across Canada. Our literature review and research findings highlight the importance of fostering youth generativity and note that youth programming supported by adult allies is a fruitful context for this task.