Outdoor play comprises a highly significant play category through which children learn, develop, express themselves, socially and physically interact with their surroundings. Research, however demonstrates outdoor play is not substantially utilized within Greek preschool environments. This study was conducted during the 2019 academic year, aiming at examining, via questionnaire, the views of current (N:100) and prospective (N:100) Kindergarten Educators regarding outdoor play's importance and utilization as a learning and development asset within Greek preschool environments. Findings establish that current and future educators acknowledge outdoor play's contribution into children's learning and development and promote natural materials playing into Kindergarten. Nevertheless, they fail to exploit exterior settings for organized play activities; prospective educators but occasionally evaluate toy-objects or the play equipment of the school yard. This study, finally, highlights the need for retraining Greek educators towards a better utilization of outdoor play and its incorporation into Kindergarten's educational process.