This article explores some diverse examples as a way of furthering the understanding of the complexities of descendant community engagement and offering some suggestions as to methodology. Several sites are investigated with a variety of levels of community engagement and all have particular historical trajectories that have often helped determine the timbre and extent of this interaction. The example sites that this article draws on include the Freedman's Cemetery and Juliette Street Projects in Dallas, Texas, the Van Winkle's Mill project in the rural Arkansas Ozark Mountains, and the site of the Rosewood Massacre in northern Florida. Each of these sites has very different community dynamics. The article demonstrates how complicated, contradictory, multifaceted, and polyvocal these things called descendant communities can be.