The transition to kindergarten represents a significant milestone in the lives of young children and their families. This period may be both exciting and challenging for families, and there are efforts that parents and educators can make to help ease difficulties that arise during the transition. Working within the framework of Bronfenbrenner’s bioecological model and the concept of academic socialization, the current study used the Early Childhood Longitudinal Study – Kindergarten Class of 1998-99 (ECLS-K) to explore the associations among transition activities, beliefs about school readiness skills, parental involvement in school-based activities, and children’s adjustment to kindergarten. Children in families with higher incomes and those speaking English at home experienced more transition activities than did their peers. Children whose families were offered a greater number of transition activities experienced a more positive adjustment to kindergarten. Additionally, families receiving more transition support were more engaged in school-based parent involvement activities during the kindergarten year. The study concludes with recommendations for additional research to understand more about how transition activities can support diverse families, and how schools and other organizations might make investments in supporting the transition between early education and kindergarten.