Since 1965, Head Start has stood as a model, two-generational program for promoting developmental competencies among children living in socioeconomic disadvantage for the US and international communities. The cornerstone of Head Start is the promotion of caregivers' involvement in their young children's development and early learning. In accomplishing this ambitious goal, Head Start operates from a variety of programming options, one of which is home-based. The home-based Head Start program can occur alone or be combined with a classroom-based program. Relative to its classroom-based counterpart, the home-based program has received little empirical attention. To this end, this study explores the association of home visiting frequency to caregiver involvement as it occurs naturally in a combined Head Start program serving families in small urban communities. The interrelationships of child and family demographics to caregiver involvement as well as participation in the home-based program were also examined. Consistent with prior studies, two-parent families reported greater involvement in the children's preschool education than other family structures. Additionally, home visiting frequency was higher for Hispanic families relative to African American and Caucasian families. Notably, home visiting frequency did not correspond with families' report of their involvement with their child at home or preschool or their communication with classroom teachers. Although the exploratory nature of this study does not yield conclusions, it does call attention to the need to empirically investigate the development and integration of evidence-based caregiver involvement interventions in the home-based Head Start program.