Continued improvements in spatial datasets and hydrological modeling algorithms within Geographic Information Systems (GISs) have enhanced opportunities for watershed analysis. With more detailed hydrology layers and watershed delineation techniques, we can now better represent and model landscape to water quality relationships. Two challenges in modeling these relationships are selecting the appropriate spatial scale of watersheds for the receiving stream segment, and handling the network or pass-through issues of connected watersheds. This paper addresses these two important issues for enhancing cumulative watershed capabilities in GIS. Our modeling framework focuses on the delineation of stream-segment-level watershed boundaries for 1:24,000 scale hydrology, in combination with a topological network model. The result is a spatially explicit, vector-based, spatially cumulative watershed modeling framework for quantifying watershed conditions to aid in restoration. We demonstrate the new insights available from this modeling framework in a cumulative mining index for the management of aquatic resources in a West Virginia watershed.