Living in Westernized society, adults are generally faced with daily challenges and responsibilities that occupy daily life that serves to reinforce only a passing connection with the natural world that humans are a part of. Although these constant and immediate demands hold one’s attention in the present, there is still a part of the subconscious that remains connect-ed to nature and remains locked in-step with daily, monthly, and seasonal rhythms. For children, the attraction towards nature and the outdoor environment exerts a powerful pull beyond the seemingly tenuous connections that may be felt superficially by adults. This is of particular importance, specifically in the arena of children’s play. The pursuit of play is enshrined within Article 31 of the United Nation’s Convention on the Rights of the Child, affirming that it is not only a crucial activity for child development, but a fundamental right (UN, 1990). What is not articulated, however, is a qualitative assessment of the kinds of play children must have available to them. In our adult sensibilities, we see play in the context of our lives as a leisure activity, something that is inherently unproductive, maybe even frivolous; it’s what we do after we have fulfilled our responsibilities and obligations and is frequently relegated for our ‘time off.’ Nothing could be further from the truth for children, and is in fact critical for their healthy physical, social, emotional, and mental development. It is also the gateway through which children learn about the world and each other, thereby making it a primary activity that enables their growth. This is especially true for outdoor play. The natural world has traditionally and historically been an environment for children’s play, within both preschool and school-age settings. Children’s exploration, experience, and experimentation with the world around them is fundamental to their physical, social, emotional, and cognitive development. For adults, play may appear in the context of their lives to be simply a leisure activity that is fun or otherwise entertaining, to the extent that many adults have forgotten how it was to play as a child. In this vein, children may be treated akin to ‘little adults’ who must be taught the ways of the world primarily through explanation, description, and academic instruction, with opportunities for play minimized or otherwise structured and under the direct control of adults. In this way, over several decades, many modern societies have systematically minimized not only the value of nature in the learning environment in its multitude of forms and opportunities, but also the critical benefits of children’s free play, or play that is not directed or structured by adults. At the same time, there has been in-creased awareness and alarm raised among healthcare providers, educators, and parents regarding a multitude of problems that children increasingly exhibit and are suffering from. These run the gamut from attention disorders, lack of physical strength and stamina, illness and disease, aggression, and other emotional issues such as anxiety and depression. In the singular drive to educate children about the world, there has been a steady cultural shift towards an impulse to insulate them through increased structure due to the devaluation of free play and fears of their safety to keep them from it. In this fact, Peter Gray states in Free to Learn that “we have here a terrible irony. In the name of education, we have increasingly deprived children of the time and freedom they need to educate themselves through their own means” (2013, p. 19). However, more recent examinations and studies have brought the attention back to the ways in which the natural world affords critical opportunities and challenges for children to explore their own abilities for physical movement, imagination, and the development of social and emotional skills. For example, studies show that when children have the opportunity for free play outdoors, it has a positive influence on their ability to problem solve and their creativity is enhanced (Hamilton, 2014). Indoor environments are fundamentally different for children in that there are specific expectations or concepts of how children should use these spaces, and indoor toys possess a more rigid or pre-designed purpose which creates limitations for play(Hanscom, 2016). The natural world of the outdoors, on the other hand, affords children a sense of freedom, inspiration, and a learning environment through their play in which they can use their bodies and imaginations with limitless possibilities. Here the visceral experiences that the world provides can be felt through a multitude of sensory inputs at once, and the actions they make in this realm strengthen and build them physically and mentally, among many other benefits. Principally, children’s social-emotional skillsets are developed through practice and frequent opportunities for play with other children, especially in an outdoor setting (Hanscom, 2016). There are many educational movements that give focus to many of the issues outlined above. One approach that maintains a unique focus and perspective on children’s development and the world they inhabit is within Waldorf education. Having originated more than a century ago in Europe, this movement has gained both increased traction and interest from parents and educators with hundreds of schools all around the world (Edwards,2002) as an independent alternative to other public or private school offerings. This project illuminates and contributes clarifying answers towards the ways in which Waldorf education is uniquely positioned within the subject of children’s play, to forge their critical developments, including social and emotional, from early childhood to the later grade school years and beyond.