The Head Start program endeavors to provide preschoolers with high-quality learning opportunities, in part through fostering family involvement. This exploratory study addressed the paucity of empirical research regarding the nature of educator outreach and family involvement in Head Start and their contributions to children's development of the academic and social foundations of literacy. Participants included 3,100 children and families enrolled in the Head Start Family and Child Experiences Survey (FACES) study, their classroom teachers (n = 286), and their center directors (n = 222). Findings revealed that families regularly engaged in the learning and schooling of their children and that Head Start educators regularly reached out to families. Family involvement and educator outreach were selectively associated with children's decoding, vocabulary, and positive approaches to learning. This study clarifies how families and teachers bridge the home-school gap in Head Start preschool programs and thus contribute to children's early literacy skills.