Healthy and high levels of physical activity can positively impact youth development, physiological and psychosocial well-being, academic performance, and reduce the risks of obesity, cardiovascular disease, and other chronic illnesses. Various health and physical activity interventions have started to engage with wearable technologies (e.g., Fitbit®) to objectively measure and manage levels of physical activity, for both academics and practitioners alike. The purpose of this study is to explore the potential utility of digital activity trackers, and the subsequent experiences of wearing such devices, toward increased engagement with physical activity among racially and economically marginalized youth. To this end, we had 20 youth of color wear a Fitbit Zip® over a 23-week period during their participation in a sport-based youth development program. At the conclusion of 23 weeks, 17 of the students reflected on their experiences by taking part in one of three focus groups. The participants shared predominantly positive experiences with and attitudes toward the devices. While there were some sentiments of indifference, most participants acknowledged increased levels of physical activity and awareness of the resultant health benefits. These results further highlight the potential value of integrating digital activity trackers in sport-based youth development programming and stress the importance of culturally appropriate expectations and training.