<p>This study investigates the evolving drought dynamics in southern Portugal, focusing on changes in drought severity, variability, and spatial patterns using two meteorological indices, consecutive dry days (CDD) and number of days with precipitation lower than 10 mm (RL10), for two consecutive 20-year periods T1 (1980–2000) and T2 (2001–2020). The stochastic simulation of these indices helps to visualize the spatial variability, local trends, and extreme behavior of drought phenomena. As the drought indices CDD and RL10 can be considered complementary indicators of the phenomenon, we created a joint drought index in the second phase of this study by integrating both indices using a multivariate approach. Then, for each monitoring station and period T1 and T2, we calculated three severity classes for CDD and RL10. Lastly, using multidimensional scaling (MDS) analysis, the different monitoring stations were represented in MDS space for the two periods T1 and T2. The spatial representation, through stochastic simulation, of one MDS factor reveals the local trends in drought from T1 to T2, highlighting the most critical local areas.</p>