Grassland regions of the southern Great Plains are fragmented by agricultural activity and many habitat remnants have experienced encroachment by juniper (Juniperus virginiana L.). Recently, many cropland areas have been converted to monoculture grassland (pastures) and enrolled into the Conservation Reserve Program (CRP). Our objectives were to develop spatial and temporal Markov models to characterize land cover dynamics relative to juniper expansion and CRP using aerial photography from 1965, 1981, and 1995. We used landscapes surrounding three Breeding Bird Survey routes with varying levels of juniper encroachment in Oklahoma as study areas. As expected, land cover changes from 1965 to 1995 included increases in juniper woodland, mixed juniper-deciduous woodland, and pastures from CRP activity. Markov models revealed that juniper had a low likelihood of self-replacement in early stages of encroachment. In all areas, relatively little native grassland was lost to juniper encroachment, but other native habitat types such as deciduous woodland were heavily impacted. Transition probabilities for land cover dynamics varied significantly both spatially and temporally. Projections of these raw transition matrices produced widely varying models of future land cover conditions. By modifying the matrices to account for recent and potential socio-political and ecological changes occurring in this region, a number of more plausible land cover scenarios were produced than those resulting from simple projections of raw transition matrices.