Aquatic scientists often require environmental information about the watersheds that drain to stream reaches of interest. Furthermore, we often need this information for many watersheds that can occur across large spatial extents (e.g., many states/provinces) thus complicating data extraction via GIS. We developed a multi-watershed delineation (MWD) tool to rapidly delineate watershed boundaries for numerous locations within geographically extensive areas from digital elevation models (DEMs). The MWD tool then outputs these delineations as ESRI shapefiles which are then overlain onto additional GIS layers to extract watershed-level information such as climate regime, soil condition, and geology type. We present an example of the delineation and characterization of several hundred watersheds that we conducted in support of stream bioassessments. The MWD tool also derives several catchment-level geomorphic features of potential hydrologic and ecological importance such as drainage density, relief ratio, hypsometric curve indices, and elevation statistics. Applying the MWD tool to watersheds that occur across a broad spatial extent requires a database of large, hydrologically-correct DEMs, and development of this database presents several challenges. We describe approaches that we developed for creating and maintaining these large datasets that aid in rapid and accurate watershed delineations with the MWD tool.