This article presents projected future drought occurrences in five river basins in Virginia. The Soil and Water Assessment Tool (SWAT) and the Coupled Model Intercomparison Project Phase 5 (CMIP5) climate models were used to derive input variables of multiple drought indices, such as the Standardized Soil Moisture index (SSI), the Multivariate Standardized Drought Index (MSDI), and the Modified Palmer Drought Severity Index (MPDSI) for both historic and future periods. The results of SSI indicate that there was an overall increase in agricultural drought occurrences and that these were caused by increases in evapotranspiration and runoff. However, the results of the MSDI and MPDSI projected a decrease in drought occurrences in future periods due to a greater increase in precipitation in the future. Furthermore, GCM-downscaled products (precipitation and temperature) were verified using comparisons with historic observations, and the results of uncertainty analyses suggest that the lower and upper bounds of future drought projections agree with historic conditions.