Twenty-first century demands students with critical thinking, digital and other soft skills, and capable of self-directed and self-determined learning. This chapter presents an educational design project, which focused on the development of a history online course for children of pre-primary level and the first grades of primary school, based on the constructivist paradigm of learning. Educational design research was carried out to explore how young children can respond to the demands of a contemporary online course, pursue the online course with growing confidence and independence, and earn history in a meaningful way, while developing twenty-first century skills at the same time. Data were collected by quantitative and qualitative methods and analysis showed that both pre-primary and primary school children responded remarkably well and managed to complete the online course with minimum parental support. They improved their knowledge and displayed critical thinking skills. Children showed no major difficulties in using the digital environment and expressed positive attitudes toward e-learning. The role of parents was also monitored and analyzed since it emerged as a critical factor in the successful completion of the course.