While the layout of plantation slave villages demonstrate a great deal of planter control, the private landscapes of enslaved peoples offer insights into the activities and experiences where the reach of the planter was more limited. Archaeological investigations of the caves and gullies surrounding St. Nicholas Abbey sugar plantation in St. Peter, Barbados offer insights into the activities that some enslaved plantation workers pursued. The gullies winding between St. Nicholas Abbey, the tenantry of Moore Hill, Pleasant Hall plantation and other estates in St. Peter contain a series of caves, many of which possess material culture, including ceramics, clay tobacco pipes, and black bottle glass. These caves, as liminal spaces on the landscape between adjoining plantations, appear to have served as meeting areas for enslaved peoples and later free workers. The privacy these spaces afforded spurred physical mobility and social interaction between enslaved peoples from surrounding villages, and may have fostered activities that were not permitted in the public sphere, such as gaming and leisure. Gullies are thus viewed as conduits and corridors that connected communities in the plantation-dominated landscape of Barbados and offered a temporary respite from the challenges of plantation life.