This study employed a novel combination of data (winter cover crop cost-share enrollment records, satellite remote sensing of wintertime vegetation, and results of Soil and Water Assessment Tool (SWAT) water quality simulations) to estimate the environmental performance of winter cover crops (WCC) at the watershed scale, from 2008 through 2017, within the Tuckahoe sub-watershed of the Choptank River. The Choptank is a river basin within the Chesapeake Bay watershed and, as a focus watershed for the U.S. Department of Agriculture’s Conservation Effects Assessment Project (CEAP), has been the subject of considerable study assessing linkages between land use and water quality. Farm enrollment data from the Maryland Agricultural Cost Share (MACS) program documented a strong increase in the use of WCC within the Tuckahoe watershed during the study period, from 27% of corn fields and 9% of soybean fields in 2008 to 89% of corn fields and 46% of soybean fields in 2016. Satellite remote sensing of wintertime ground cover detected increased wintertime vegetation following corn crops, in comparison to full season and double cropped soybean, consistent with patterns of cover crop implementation. Although inter-annual variation in climate strongly affected observed levels of vegetation, with warm winters resulting in increased vegetative cover, a 30-year analysis of wintertime greenness revealed significant increases in wintertime vegetation associated increased adoption of WCC. The predominant WCC species recorded by the MACS program as planted in the Tuckahoe watershed were wheat (68.1%), barley (16.1%), and rye (7.2%). The MACS WCC enrollment data were combined with output from the SWAT model, calibrated to streamflow and nutrient loading from the Tuckahoe watershed, to estimate water quality impacts based on known distribution of cover crop species and planting dates (2008 to 2017). Results indicated a 25% overall 10-year reduction in nitrate leaching from cropland resulting from cover crop adoption, rising to an estimated 38% load reduction in 2016 when 64% of fields were planted to cover crops. A large portion of WCC (39.3%) were planted late (after October 15) and planted to wheat (68.1%). Increased environmental benefits would be achieved by shifting agronomic methods away from late-planted wheat.