Transit spaces are not uniformly experienced by their users. Closer inspection of individuals’ journeys reveals unique barriers corresponding with race, gender, age and ability, signifying that the mobility of certain groups may be less accessible than that of more privileged groups. Using the frameworks of a “politics of mobility” (Cresswell 2010) and “mobility injustice” (Sheller 2018), this paper examines the transit needs and experiences of female caregivers and youth populations whose mobilities are frequently challenged. I engage with the following questions: How do mothers and children in Philadelphia conceptualize accessibility of transit infrastructure? What are the differences and similarities between the concerns of mothers and their children regarding mobility practices? How do transit agencies currently account for the mobility needs of mothers and children? How do mothers, children, and transit officials conceptualize a family-friendly transit system? How can robust community engagement enhance transportation planning practices in the future? I find that the experiences of mothers and children navigating transit spaces center around the themes of safety, comfort and convenience. In particular, mothers’ express challenges regarding street safety, gendered treatment in public space, and inconvenience of travelling with young children. Children underscore their concerns about safely navigating their neighborhoods in light of reckless driving, issues of poor sanitation and the presence of strangers, and the desire to make transportation spaces sites of play and fun. Mothers and children also expressed clear ideas about how to improve transportation infrastructure to better meet their needs. While planning initiatives and engagement strategies that mitigate certain challenges faced by mothers and children do exist, work is needed to enhance the user experience. Community engagement is a vital component to the creation of not just a family-friendly transportation system, but also one that is accessible to all.