Little is known about the beneficial outcomes (e.g., experiential benefits sought and achieved, place meanings) and environmental setting preferences across varying recreation areas. The purpose of this study is to better understand differences in the experiential recreation outcomes and setting preferences of Florida National Scenic Trail hikers by segmenting and comparing two groups based on the type of natural area they hiked: wildland–urban interface (WUI) visitors and wildland visitors, somewhat equivalent to the Recreation Opportunity Spectrum (ROS) construct. This study utilized physical development density criteria (i.e., percent natural vegetation coverage, housing density per acre) obtained from a Geographic Information Systems (GIS) database for the recreation setting classification. The wildland visitor group had stronger preferences for achievement and environmental exploration benefits and for more natural settings, while mental and physical health/wellness and in-group social bonding benefits were equally important for both groups. Ecological integrity was ascribed more strongly by the wildland group, and WUI visitors more strongly identified with the community identity construct. These results verify most ROS precepts and show that varying ROS type settings provide experiential outcome opportunities consistent with ROS parameters, though some refinements for WUI settings were identified.