Early childhood drawings reveal what young children see, know, feel, and think. The purpose of this study was to explore the relationship between the development of creative expression in early childhood drawings and the cultural and personal context of the production of the drawings. In this study, 750 pieces of drawing by a six-year child were observed and twenty eight drawing portfolios compiled over six months were analyzed. The authors used contextual inquiry and observation, and found a significant relationship between creative expression and personal and cultural factors that inspired the young child’s drawings. Four stages of drawing learning were identified, namely conscious stage, alternative stage, free stage and integrated stage. Topics and images of the child’s creative expression were affected by personal and cultural factors at different stages. The effect of personal and cultural factors on four stages of drawing tracks are discussed. This research suggests that the quality of the personal and cultural experiences at differential drawing stages are likely to be of great benefit in improving the creativity of young children.