English Heritage Trust (EH) prides itself on communicating the histories of its sites through playful forms of engagement. In the recent scholarship of EH heritage managers David Sheldon (2011), Joe Savage, and William Wyeth (2020), new forms of creating play and providing site histories are considered alongside the challenges of updating signage and activities to meet visitor expectations. Expanding castle narratives beyond the Norman origins, increasing representations of women and lesser-known historic figures, and addressing the domestic function of castles are a priority for Sheldon, Wyeth, and Savage as they create case-by-case programs for their many properties. This paper considers what pedagogical methodologies are utilized at EH’s Conisbrough Castle, the selected story for presentation and why, and what display methods can be expanded to add to the visitor understanding of Conisbrough’s longer story through the Middle Ages. Using a mix of display boards, video, and text-based signage, managers at Conisbrough recall the de Warenne family narrative and recognize the Conisbrough keep’s domestic function. This is a successful recollection of this one resident’s story, however, only featuring this narrative limits Consibrough’s history to the Norman period. As EH seeks to grow their castle histories, I propose creating new engagements through the current display media that emphasize the importance of multiple tenant stories across time in castle spaces. Increased opportunities to relate to the past and retain information through play will assist visitors as they come to recognize the home as witness to both domestic activity and those events that occurred on the world stage.