Piñon pine and juniper woodlands in the southwestern United States are often represented as an expanding and even invasive vegetation type, a legacy of historic grazing, and culpable in the degradation of western rangelands. A long-standing emphasis on forage production, in combination with recent hazard fuel concerns, has prompted a new era of woodland management with stated restoration objectives. Yet the extent and dynamics of piñon–juniper communities that predate intensive Euro-American settlement activities are poorly known or understood, while the intrinsic ecological, aesthetic, and economic values of old-growth woodlands are often overlooked. Historical changes in piñon–juniper stands include two related, but poorly differentiated processes: recent tree expansion into grass- or shrub-dominated (i.e., non-woodland) vegetation and thickening or infilling of savanna or mosaic woodlands predating settlement. Our work addresses the expansion pattern, modeling the occurrence of “older” savanna and woodland stands extant prior to 1850 in contrast to “younger” piñon–juniper growth of more recent, postsettlement origin. We present criteria in the form of a diagnostic key for distinguishing “older,” pre-Euro-American settlement piñon–juniper from “younger” (post-1850) stands and report results of predictive modeling and mapping efforts within a north-central New Mexico study area. Selected models suggest a primary role for soil moisture in the current distribution of “old” vs. “young” piñon–juniper stands. Presettlement era woodlands are shown to occupy a discrete ecological space, defined by the interaction of effective (seasonal) moisture with landform setting and fine-scale (soil/water) depositional patterns. “Older” stands are generally found at higher elevations or on skeletal soils in upland settings, while “younger” stands (often dominated by one-seed juniper, Juniperus monosperma) are most common at lower elevations or in productive, depositional settings. Modeling at broad regional scales can enhance our general understanding of piñon–juniper ecology, while predictive mapping of local areas has potential to provide products useful for land management. Areas of the southwestern United States with strong monsoonal (summer moisture) patterns appear to have been the most susceptible to historical woodland expansion, but even here the great majority of extant piñon–juniper has presettlement origins (although widely thickened and infilled historically), and old-growth structure is not uncommon in appropriate upland settings.