This paper reports findings from a longitudinal follow-up of close to 1300 children. Observation data were collected from preschool (49 classrooms) and 1st grade (32 classrooms) using the Early Childhood Classroom Observation Measure (ECCOM; Stipek & Byler, 2005) and the Classroom Assessment Scoring System (CLASS; Pianta, La Paro, & Hamre, 2008). In the present analyses we report on the predictive relationships between indicators of classroom quality as assessed by the ECCOM and the CLASS measures, and children’s preschool and 1st grade motivation and academic achievement. In a set of analyses using multilevel modeling on the CLASS measures we found that high classroom organization and low self-reported teacher stress predicted high learning motivation in children, and that children’s learning motivation contributed to their level of phonological awareness, whereas high instructional support contributed to low levels of avoidant strategies among children in the classroom and their math skills. Analyses on the ECCOM measures showed that in classrooms in which the teachers showed a high level of child-centered teaching practices, the children showed higher task motivation in reading and mathematics. Maternal education did not emerge as a significant predictor but child gender had an effect on motivation and learning outcomes.