Using data from the Head Start Family and Child Experiences Survey 2009 Cohort, this study investigated the school readiness trajectories of 2,908 Head Start children from Head Start to kindergarten. Multilevel growth curve models examined differences by immigrant-origin status and the moderating role of enriching experiences. Research Findings: Immigrant-origin children demonstrated lower language and math skills at Head Start entry. However, the differences narrowed over time by accelerated gains in skills. Also, moderation analyses suggested that higher levels of enriching experiences, including community-based activities and family history/ethnic heritage talk, could potentially contribute to the school readiness of immigrant-origin children. Practice or Policy: Findings underscore that family resources may have implications for alleviating unequal opportunities and outcomes for immigrant-origin children, in particular.