Western juniper (Juniperus occidentalis Hook.) woodlands have persisted for millennia in semiarid parts of the northern Great Basin, USA, providing critical habitat for plant and animal species. Historical records suggest that the establishment of western juniper is strongly associated with regional climatic variability. For example, the abundance of western juniper pollen and macrofossils measured in lake sediment cores increased rapidly in the mid-1500s, concurrent with a regional increase in winter precipitation. However, little is known about how climatic factors interact with landscape structure to control the spatial distribution of western juniper at fine scales and at lower treelines. We used tree rings to reconstruct a spatially distributed history of establishment for 421 western juniper trees across 130 ha on Horse Ridge in central Oregon. Establishment occurred between 845 and 1961 CE, but most trees established after the mid-1550s. The pronounced sixteenth century pulse of establishment represents a transition from more open wooded shrublands to persistent woodlands and coincides with an increase in cool-season moisture and generally cool summer temperatures. Ancient trees that established before this were limited to certain microsites, suggesting that local topoedaphic conditions influenced juniper woodland demography and distributions, although we could not identify consistent environmental drivers. In the future, warmer and drier growing season conditions and a potential increase in wildfire activity may broadly limit western juniper recruitment and its distribution across the region, but at finer scales landscape features that buffer climate change impacts or provide fire safe niches may serve as refugia.