This study investigated the relationship of cultural and educational contexts and the development of pretend play in toddlers from an ethnographical approach between two cultures, namely the United States and Korea. For the purposes of data analysis, units of activity were used and the social interactions of each activity were then organized. The common themes in evidence within both cultures were then interpreted. There were many similarities in terms of pretend play between the two cultures. However, there were also some differences in pretend play in evidence. These differences were seen in terms of play which revolved around fantasy play as well as play related to social development, both of which are areas which were influenced by the roles of teachers.