In response to novel and complex uncertainties, the present research is conducted to characterize the most significant indicators of watershed health including drought, water quality, and vegetation for the Tajan watershed, Mazandaran, Iran. The Standardized Precipitation Index (SPI) and Streamflow Drought Index (SDI) are, respectively, used to quantify the meteorological and hydrological droughts in the present (1993–2020) and future (2023–2050) employing optimistic RCP2.6 and pessimistic RCP8.5 scenarios. To concoct discharge data for the future, IHACRES v1.0 software is used with a Nash–Sutcliffe coefficient (NSE) of 0.48 and a coefficient of determination (R2) of 0.58. Maps of land use and Normalized Difference Vegetation Index (NDVI) are also prepared using Landsat images. Subsequently, the surface water quality is assessed using AqQA v1.1.0 software. The results show the difference in the severity of future meteorological droughts in different stations. In addition, the predominance of non-drought (SDI ≥ 0) or mild drought (−1 ≤ SDI < 0) is indicated for future hydrology. The land use changes show a decrease in rangeland (−5.47%) and an increase in residential land (9.17%). The water quality analysis also indicates an increase in carbonate ions in the watershed outlet. Communicating the relationships between study indicators, which is a big gap in the current watershed management approach, avoids future failures and catastrophes.