In the United States, visitors to heritage sites have been steadily declining, and in the wake of this phenomenon, these sites have often turned to edutainment as a way to diversify methods to earn diminishing revenue in an increasingly competitive heritage tourism market. The term edutainment is a portmanteau (education/entertainment) signifying the tendency of controlling stakeholders of cultural institutions to infuse elements of entertainment into their presentations in an attempt to attract new audiences. Plantations, important heritage sites in the US South, have generally been reluctant to engage in meaningful discussions of slavery. Using the framework of edutainment and affect and emotion, this chapter will specifically explore the growing plantation edutainment complex and ultimately how this competes with creating affective/emotional encounters with slavery and enslaved persons. Plantation management seeks to create a variety of experiences for visitors (through tours, a diversification of land use on the plantation itself) that will make their site stand out from the competition and appeal to a broader range of tourists. The resulting multitude of entertainment options, as well as pressures on tour guides to entertain their audiences, leads to the elision of the trauma and pain associated with slavery that took place within these landscapes.