In two related field studies: (1) a multiscale riparian forest inventory and (2) a comparative study of natural forest gap and nongap environments, we explored regeneration patterns of native riparian trees in relation to large- and small-scale ecological drivers in four western Oregon watersheds spanning a climatic gradient from dry to wet. Twenty-three tree species were classified by life history traits into five functional groups that differed in shade and drought tolerance; distribution and abundance of tree regeneration were analyzed by group. For most groups, seedling abundance varied substantially across the large scale climate gradient. In particular, drought tolerant species decreased sharply in abundance from the drier to wetter watersheds. Overall seedling frequency and diversity also decreased from the driest to wettest watersheds, while nurse log use increased. Regeneration of most, but not all, species was greater in gaps. Principal conclusions are that life history information was useful for categorizing species and quite predictive of regeneration behavior overall, yet for many species contextual factors such as climate, forest structure, and adjoining species were also very important. Species appeared to regenerate opportunistically wherever local conditions fell within their environmental tolerances and competitive abilities. Management or restoration of riparian forests, therefore, requires knowledge of site conditions, the life history of the riparian trees present, and in particular an understanding of the species’ environmental tolerances, disturbance responses, and competitive abilities relative to one another.