This study aims to develop an approach to characterize cropland drought conditions in El Salvador, Central America. The data were processed for 2016–2017 through three main steps: (1) reconstructing MODIS land-surface temperature (LST), (2) Landsat-MODIS data fusion and (3) drought delineation using the temperature vegetation dryness index (TVDI). The results of LST reconstruction using the random forests (RF) indicated the median RMSE value of 0.5 °C. The fusion results achieved from the STARFM compared with the reference Landsat data revealed close agreement with the correlation coefficient (r) values higher than 0.84. The TVDI results verified with that from the reference Landsat data indicated r values of 0.85 and 0.75 for 2016 and 2017, respectively. The larger very dry area was observed for the 2016 primera season due to prolonged droughts. Approximately 11.5% and 10.7% of croplands were, respectively, associated with very dry moisture condition in the 2016 and 2017 primera seasons.