Drought, as an extreme climatic event, is considered one of the most severe natural disasters worldwide. In Northeast Asia, the frequency and intensity of drought have been exacerbated by climate change, causing significant negative impacts on the region’s socioeconomic conditions and agricultural production. This study analyzed the spatiotemporal evolution and trends in drought in transboundary river basins in Northeast Asia from 1990 to 2020, using meteorological station data and remote sensing data. The Standardized Precipitation Evapotranspiration Index (SPEI) and Vegetation Condition Index (VCI) were employed to assess drought characteristics, and a comprehensive analysis of the SPEI and VCI indices was conducted to evaluate drought severity under different land cover types. The results indicate that (1) in the past two decades, both the SPEI and VCI indices have shown an increasing trend in the basin, with moderate and mild droughts being predominant. (2) High and extreme droughts mainly occur in forest areas, accounting for 17.91% and 10.76%, respectively, followed by farmland.