In a notoriously cold-seasoned region, this paper explored how our formal education and non-formal environmental education (EE) gatekeepers of Northeastern Minnesota regard the importance of outdoor play and cold weather for young students. This research study explored the relationship between participant gatekeepers' beliefs of the benefits outdoor play and beliefs toward cold weather. Using online survey research, this descriptive study found both formal and non-formal EE educational communities to have overall, positive beliefs toward the benefits of outdoor play, however, significant differences between formal education gatekeepers and non-formal EE gatekeepers' beliefs toward cold weather emerged. Results from this study point toward differences between the institutional influence of formal and non-formal EE, and invite discussion for possible implications on early childhood students' opportunities for outdoor play in cold weather. Strategies for educational gatekeepers were also presented to support early childhood opportunities for outdoor play in cold weather, fostering year-round well-being and resilience of young students.