San Miguel Island is the westernmost of the California Channel Islands and one of the windiest areas on the west coast of North America. The majority of the island is covered by coastal sand dunes, which were stripped of vegetation and subsequently mobilized due to droughts and sheep ranching during the late 19th century and early 20th century. Since the removal of grazing animals, vegetation and biological soil crusts have once again stabilized many of the island's dunes. In this study, historical aerial photographs and field surveys were used to develop a chronosequence of the pattern of change in vegetation communities and biological soil crust levels of development (LOD) along a gradient of dune stabilization. Historical aerial photographs from 1929, 1954, 1977, and 2009 were georeferenced and used to delineate changes in vegetation canopy cover and active (unvegetated) dune extent among 5 historical periods (pre-1929, 1929–1954, 1954–1977, 1977–2009, and 2009–2011). During fieldwork, vegetation and biological soil crust communities were mapped along transects distributed throughout San Miguel Island's central dune field on land forms that had stabilized during the 5 time periods of interest. Analyses in a geographic information system (GIS) quantified the pattern of changes that vegetation and biological soil crust communities have exhibited on the San Miguel Island dunes over the past 80 years. Results revealed that a continuing increase in total vegetation cover and a complex pattern of change in vegetation communities have taken place on the San Miguel Island dunes since the removal of grazing animals. The highly specialized native vascular vegetation (sea rocket, dunedelion, beach-bur, and locoweed) are the pioneer stabilizers of the dunes. This pioneer community is replaced in later stages by communities that are dominated by native shrubs (coastal goldenbush, silver lupine, coyote-brush, and giant coreopsis), with apparently overlapping or cyclical succession pathways. Many of the dunes that have been stabilized the longest (since before 1929) are dominated by exotic grasses. Stands of biological soil crusts (cyanobacteria) are found only on dunes where vascular vegetation is already present. Biological soil crusts are not found on dunes exhibiting a closed vascular plant canopy, which may indicate that the role of soil crusts in dune stabilization on the island is transitory. Particle-size analyses of soil samples from the study area reveal that higher biological soil crust LOD is positively correlated with increasing fine grain content. The findings indicate that changes in vegetation communities may be the most rapid at earlier and later stages of dune stabilization and that regular monitoring of dunes may help to identify the interactions between vegetation and soil crusts, as well as the potential transitions between native and exotic plant communities.