Historically, oak woodlands of northern California have been subject to intensive tree and brush removal efforts to improve land for livestock grazing. As a result of this tree removal, these watersheds are susceptible to soil erosion and stream degradation. Therefore, planting woody vegetation is often required to restore watershed function. Prior to such actions, a thorough understanding of natural vegetation regeneration patterns is essential. The physical and biological attributes of natural vegetation regeneration in a cleared watershed were characterized using remote sensing, a Geographic Information System, and field surveys. A 79-ha watershed at the University of California's Hopland Research and Extension Center was examined because the clearing of vegetation was part of a well-documented experiment in the early 1960s, providing essential baseline data. The results of this study reveal that significantly more oak regeneration, consisting mostly of evergreen oaks, occurred on moister and steeper northerly slopes. Deciduous oaks, located primarily on drier and less steep southerly slopes, have not regenerated. Hardwood regeneration was associated with Josephine, Los Gatos, and Maymen soils. The distribution of hardwood regeneration is clustered, suggesting that the presence of other trees may promote regeneration. These results also suggest that without active restoration efforts such as tree planting and seedling protection, southerly slopes will most likely remain barren and erosion will continue, while northerly slopes and riparian areas will recover under the current land management practices. Despite some woody plant regeneration, the once densely forested watershed is now predominantly grassland, emphasizing the need to minimize clearing of California oak woodlands.