Young adults with intellectual and developmental disabilities (IDD) are vulnerable to transportation challenges which can contribute to a lack of community engagement. This article describes findings from a qualitative study in which we conducted one time, semistructured interviews with nine individuals with IDD (ages 18--25) and their parents/guardians in dyads. We also interviewed 10 adult service and local agency providers to incorporate different perspectives. Major themes included "family factors," "community structure," and "systems challenges" as barriers that impacted the transportation experiences of young adults with IDD and their families. We provide implications for transition-related professionals and suggestions for future research and policy focused on transportation.