The growing number and effectiveness of Earth observation satellite systems, along with the increasing reliability of remote sensing methodologies and techniques, present a wide range of new capabilities in monitoring and assessing droughts. A number of drought indices have been developed based on NOAA-AVHRR data exploiting the remote sensing potential at different temporal scales. In this paper, the remotely sensed Reconnaissance Drought Index (RDI) is employed for the quantification of drought. RDI enables the assessment of hydro-meteorological drought, since it uses hydrometeorological parameters, such as precipitation and potential evapotranspiration. The study area is Thessaly, central Greece, which is a drought-prone agricultural region characterized by vulnerable agriculture. Several drought features are analyzed and assessed by using monthly RDI images over the period 1981–2001: severity, areal extent, duration, periodicity, onset and end time. The results show an increase in the areal extent during each drought episode and that droughts are classified into two classes, namely small areal extent drought and large areal extent drought, respectively, lasting 12 or 13 months coinciding closely with the hydrological year. The onset of large droughts coincides with the beginning of the hydrological year, whereas the onset of small droughts is in spring. During each drought episode, the maximum occurs usually in the summer and they all last until the end of the hydrological year. This finding could justify an empirical prognostic potential of drought assessment.