This chapter will examine ways in which the moon is portrayed as an iconic symbol in two examples of children’s literature. Mirroring the different phases of the moon and its constant transformation, the texts selected for this chapter are written for two very different phases of a child’s life—early years and adolescence. Exploring the significance of the moon through a picture book for early childhood, Chae Strathie’s The Loon on the Moon, will emphasise the playful, positive depiction, and its role in igniting the imagination of young children. Through the inclusion of brightly illustrated aliens and wondrous planets, this picture book urges children to place their faith in imagination and the power of storytelling and play. The second text studied, J. K. Rowling’s Harry Potter and the Prisoner of Azkaban, is targeted towards an older childhood/adolescent audience, and in many ways is one which explores the darker side of the moon. Analysis of this second novel will explore relationships between the moon portrayed in a more sinister light, physical and emotional transformation, and the role of this symbol in werewolf transformation. Furthermore, through highlighting magical creatures present in the novel such as Dementors and Boggarts, Rowling is able to explore light and darkness and reflect the turbulent state of ageing and adolescence through the chaos and uncertainty surrounding a multitude of threatening figures and the curse of lycanthropy.