Changes in land cover throughout the Chesapeake Bay watershed, accompanied by variability in climate patterns, can impact runoff and water quality. A study was conducted using the Soil and Water Assessment Tool (SWAT) for the James River watershed in Virginia, the southernmost tributary of the Chesapeake Bay, from 1986 to 2018, in order to evaluate factors that affect water quality in the river. This research focuses on statistical analysis of land use, precipitation, and water quality indicators. Land cover changes derived from satellite imagery and geographic information system (GIS) tools were compared with water quality parameters throughout that timeframe. Marked decreases in forest land cover were observed throughout the watershed, as well as increased residential development. Our findings suggest strong links between land cover modification, such as residential development, and degraded water quality indicators such as nitrogen, phosphorus, and sediment. In addition, we note direct improvements in water quality when forest land areas are preserved throughout the watershed.