The exploratory study focused on describing typical routines of preparing for winter outdoor play with preschool children and their teachers. Naturalistic observations, interviews and photographs resulted in extensive examples of children's development in cognitive understanding of winter and winter-related concepts. Observations of teachers and assistants revealed task-oriented perspectives including detailed strategies and planning. Asynchronous communication and directive language were typical of teacher/child communication. Photo analyses confirmed physical skills used by preschoolers to accomplish dressing tasks and extensive curricular changes to indoor environments.