Mining of bentonitic clays in the Cretaceous Belle Fourche Shale northwest of Belle Fourche, South Dakota, began during the 1920s. Areas where mining predated regulations requiring site reclamation are characterized by a unique landscape of unvegetated spoil mounds interspersed with water-filled pits. Topsoil in the disturbed areas is largely lost, and vegetation is absent or sparse. The post-mining landscape changes represent a permanent departure from pre-disturbance conditions, making a return to a historical reference state unattainable as a restoration goal. We evaluate the potential for restoration of hydrologic connectivity to promote the development of vegetation communities and riparian habitats. To assess hydrologic connectivity and riparian habitat, we initially analyzed half-meter USDA National Agricultural Imagery Program (NAIP) visible and near infrared (VNIR) imagery to classify open water, vegetation type, and bare ground. The initial classification appropriately separated riparian from other vegetation types and the percentage of bare ground. Initial difficulty in classifying open water pixels due to suspended sediments being identified as bare ground. We revised the initial training data and post-classification interpretation of imagery. From our initial classification, we subset the area and, in July of 2025, flew a Wingtra Gen II fixed-wing drone with a Micasense RedEdge-P multispectral camera at 7 cm pixel resolution over 2 weeks, covering approximately 15 square kilometers, producing a higher-resolution multispectral dataset and a photogrammetric digital elevation model for analysis. We applied the same classification methodology to the Drone dataset results were similar. However, the higher-resolution drone data also identified regions along gullies and rills where vegetation was observed and field-checked, indicating soil development and moisture retention. Finally, we used the drone-identified riparian vegetation locations, the slope derived from the drone-based DEM, and field observations to assess riparian vegetation development as a function of slope, hydrologic connectivity, and shoreline structure. We found that slope, shoreline structure, including hydrologic connectivity, and prevalent wind direction influenced riparian vegetation development. An understanding of how slope and hydrologic connectivity influence vegetation (riparian, mesic, and upland) will allow us to suggest cost-effective approaches for long-term remediation of the bentonite mining area and potentially other similar locations regionally and globally.