Juniperus virginiana-Quercus muehlenbergii woodlands form isolated, rare communities limited to calcium-rich cliffs and rock outcrops within the larger matrix of Quercus-Carya forests in the central and southern Appalachians. The objective of this paper was to identify compositional, environmental, and age changes across the ecotone between a woodlands community and an adjacent forest at Pedlar Hills Natural Area Preserve, Virginia. We established eight belt transects from the Juniperus virginiana-Quercus muehlenbergii woodlands into the surrounding Quercus-Carya forest. All trees within transects were identified and cored to determine age. We determined soil depth, percent rock cover, slope, and aspect and recorded the location and species of all cut stumps. The woodland-forest ecotones that appeared to be relatively static were all located along physical boundaries such as ridgelines or rivers. In areas lacking physical boundaries, the forest-woodlands ecotone has shifted in the past 50 years. The Quercus-Carya forest appears to have been more successful than the woodlands community in regeneration following logging in the mid-1900s; this shift in community may have been facilitated by fire suppression. These results imply that conservation managers need to be aware of the spatial differences in community stability and concentrate their conservation efforts on community boundaries that lack physical barriers to plant invasion.