This study addresses the pressing issue of nonpoint source water pollution in Kentucky, particularly associated with large-scale agriculture. Centered on the outer bluegrass region of Central Kentucky, the research examines the water quality of headwater streams during the agricultural season. The approach involves geospatial land cover classification using aerial imagery. Water quality data were collected during the agricultural growing season from May to October 2018. Land cover classification utilized ERDAS Imagine 2016 and ESRI ArcGIS 10.6 GIS software, while conventional water quality parameters were measured with a YSI ProDSS® multiparameter water probe and a Marsh-McBirney Flo-Mate 2000 flow meter. Statistical analyses show significant differences in stream water chemistry, suggesting the impact of agricultural nonpoint source pollution. Forested streams exhibited more varied conditions, indicating a potentially better environment. As agricultural land percentage increased, water chemistry variation suggested a measurable threshold for changes. Significant differences in water quality between agricultural and forested streams highlight the potential benefits of expanding riparian zones beyond regulations. Enlarging these zones is proposed as a strategy to mitigate nonpoint source pollution in Kentucky’s waterways.