Cross-sectional research suggests associations between enrichment and cognitive skills in toddlerhood. There are no prospectively designed longitudinal studies that investigate the link between early home literacy activities and subsequent mechanisms that explain the putative cognitive benefits. This study tests long-term associations between toddler literacy enrichment and later student engagement across key academic transitions, from kindergarten to the end of high school. Using the Quebec Longitudinal Study of Child Development (QLSCD) population-based birth cohort data, we examined whether parent-reported experiences of shared reading, looking at picture books or illustrated stories, and pretend writing at age 2 years predict later teacher- and self-reported student engagement at ages 6, 12, and 17 years. The results from multiple regression models, stratified by sex and adjusted for pre-existing and concurrent child and family characteristics, revealed significant associations between early literacy enrichment and later engagement. For boys and girls, literacy enrichment in toddlerhood predicted increases in classroom engagement from kindergarten to the end of high school. These findings highlight the lasting influence of early literacy exposure on subsequent learning-related behaviors, both in and beyond the classroom. They underscore the importance of promoting enrichment in early childhood as a family strategy toward individual readiness to learn, a cornerstone of crystalized intelligence.