Every five years, the town of Kassel, Germany hosts the contemporary art exhibition, documenta, an event that is a product of the post-WWII period and which began as a reaction against Nazi-era visual politics. In the early nineteenth century in the same town, the Brothers Grimm collected the fairy tales for which they are famous, and published Children’s- and Household Tales. This dissertation reads the disparate histories of these two major institutions of Kassel together in order to explore how documenta itself functions as a kind of fairy tale – one that both transforms and haunts, and has the potential to rehabilitate but also to harm. Employing an experimental historiography that draws from both the historical methods of artists and fairy tales, this dissertation argues that the fairy tale themes of magic, transformation, and repetition are integral to documenta – an event that is rooted in trauma and recovery. This project is thematic in its approach, and as such is not meant to serve as an exhaustive overview of documenta, nor does it endeavor to catalogue every occurrence of fairy tale art that has been present at the event. Rather, it brings two disparate bodies of literature into conversation with each other. Additionally, the artwork case studies that each of the chapters are based upon are not based upon pre-existing fairy tales, but this dissertation argues the artworks function as fairy tales. Chapter 1 examines the relationship between the first documenta in 1955 and the Nazi exhibition, “Degenerate Art” from 1937, in order to examine the curatorial innovations and shortcomings that undergird documenta. Chapter 2 looks at Joseph Beuys’s monumental environmental artwork 7000 Oaks and interprets it as a work that, through its metamorphosis, promotes both mourning and regeneration. Chapter 3 seeks out the ghosts that haunt Kassel and non-teleological forms of storytelling, through the case study of Stan Douglas’s Suspiria. Chapter 4 takes Mariam Ghani’s A Brief History of Collapses to think through both documenta’s relationship with iconoclasm and an enchanted, repetitive form temporality that allow it to imagine better possible futures and radical forms of empathy.