Since its inception in 1965, Head Start has provided low-income families with wraparound early childhood programming. Serving nearly a million children and families nationwide, Head Start's "Whole Child" philosophy was particularly evident during COVID-19 when families faced unprecedented disruptions at home, school, and work. Utilizing qualitative interviews with 20 Head Start Directors from multiple regions in Illinois and across two different time-points, this study aims to identify the resources that Head Start programs provided for families during COVID-19, and describe the challenges they faced. Findings revealed that all Head Start centers provided families with basic need resources, while some, through community partnerships and grantee relationships, were able to secure additional funding to allocate cash awards for families in more dire need. Using technology needed for remote learning was a challenge for staff, teachers, and families, and many Directors expressed that their ability to continue meeting the needs of children with special needs during closures was less than ideal. Our findings highlight the critical role that Head Start plays for families and ways that practice can be improved in non-pandemic times.