This study utilizes a sociocultural approach to explore how pre-service elementary teachers’ experiences in both outdoor and formal school settings have contributed to their intentions for taking their students outdoors and perceived obstacles to doing so. The participants were pre-service elementary teachers (N = 95) enrolled in an elementary science education methods course at a public university in the Midwestern United States. This study builds on the qualitative research methodology established in a prior research study, whereby after reading Richard Louv’s book entitled Last Child in the Woods, pre-service teachers completed written essay responses to prompts about their past outdoor experiences, their intentions for taking their students outdoors, and additionally in this study, perceived obstacles to doing so once they become teachers. Analysis of the data indicates the importance of participants’ youth experiences in the outdoors and positive intentions for taking students outside. In addition, findings describe major obstacles discussed by pre-service teachers, and we use sociocultural theory to analyse the context of these findings. Implications for teacher educators working to better equip pre-service teachers to overcome these perceived obstacles are discussed.