This study examined the literacy trajectories of 185 Head Start-eligible Black children from preschool to first grade enrolled in a high-quality early learning program physically connected to an elementary school where they attended kindergarten and first grade. Social emotional, language, and literacy skills were assessed in the fall and spring of the school year in preschool and prekindergarten (PreK) and the fall only in kindergarten and first grade. Children made literacy and language gains in early childhood that were maintained into first grade. Although children in the connected early learning/elementary experience performed above peers on language and literacy skills, only differences in language skills reached significance. Advantages in kindergarten were gone by first grade as comparison children evidenced improvement of language skills that narrowed the performance gap. Findings point to the importance of creating clear academic pathways for young learners that prioritize instructional opportunities designed to maintain positive learning trajectories.