A unique, multi-tiered approach was applied to map crop-residue cover on the Eastern Shore of the Chesapeake Bay, United States. Field measurements of crop-residue cover were used to calibrate residue mapping using shortwave infrared (SWIR) indices derived from WorldView-3 imagery for a 12-km × 12-km footprint. The resulting map was then used to calibrate and subsequently classify crop residue mapping using Landsat imagery at a larger spatial resolution and extent. This manuscript describes how the method was applied and presents results in the form of crop-residue cover maps, validation statistics, and quantification of conservation tillage implementation in the agricultural landscape. Overall accuracy for maps derived from Landsat 7 and Landsat 8 were comparable at roughly 92% (+/− 10%). Tillage class-specific accuracy was also strong and ranged from 75% to 99%. The approach, which employed a 12-band image stack of six tillage spectral indices and six individual Landsat bands, was shown to be adaptable to variable soil-moisture conditions—under dry conditions (Landsat 7, 14 May 2015) the majority of predictive power was attributed to SWIR indices, and under wet conditions (Landsat 8, 22 May 2015) single band reflectance values were more effective at explaining variability in residue cover. Summary statistics of resulting tillage class occurrence matched closely with conservation tillage implementation totals reported by Maryland and Delaware to the Chesapeake Bay Program. This hybrid method combining WorldView-3 and Landsat imagery sources shows promise for monitoring progress in the adoption of conservation tillage practices and for describing crop-residue outcomes associated with a variety of agricultural management practices.