This cross-sectional research was conducted to probe how 626 Taiwanese children's conceptions of learning differ by age and gender via drawing. Participants were from the kindergarten, the first grade, and the third grade. A coding scheme categorizing the people, learning domain, and place in the drawings was developed. Chi-square tests were then performed to examine the associations among the children's three grade levels, gender, and three categories: people, learning domain, and place. The findings showed that the kindergarteners tended to draw more family members as well as family and outdoor scenes, while the third graders tended to draw more school figures as well as classroom and school outdoor scenes. The first graders drew more peers than the third graders did. The kindergarteners drew significantly more social, informal, and playful activities than the other two groups did. The place for literacy learning switched from school (kindergarteners and first graders) to home (third graders). No gender difference was identified. This study provides insight into developing curricula that smooth children's transition from kindergarten to elementary school.