The assessment of drought conditions is important in forestry because it affects forest growth and species diversity. In this study, temporal variability and trends of precipitation (P), potential evapotranspiration (PET), and their relationship (P/PET) were examined in two selected forest ecosystems that present different climatic conditions and vegetation types due to their location and hypsometric zone. The study area includes the forests of Pertouli and Taxiarchis, which are managed by the Aristotle University Forest Administration and Management Fund. The Pertouli is a coniferous forest in Central Greece with a maximum elevation of 2073 m a.s.l, and Taxiarchis is a broadleaved forest in Northern Greece with a maximum elevation of 1200 m a.s.l. To accomplish the goals of the current research, long–term (1974–2016) monthly precipitation and air temperature data from two mountainous meteorological were collected and processed. The PET was estimated using a parametric model based on simplified formulation of the Penman–Monteith equation rather than the commonly used Thornthwaite approach. Seasonal and annual precipitation, potential evapotranspiration (PET), and their ratio (P/PET) values were subjected to Mann–Kendall tests to assess the possible upward or downward trends, and Sen’s slope method was used to estimate the trends magnitude. The results indicated that the examined climatic variables vary greatly between seasons. In general, negative trends were detected for the precipitation time series of Pertouli, whereas positive trends were found in Taxiarchis; both were statistically insignificant. In contrast, statistically significant positive trends were reported for PET in both forest ecosystems. These circumstances led to different drought conditions between the two forests due to the differences of their elevation. Regarding Pertouli, drought trend analysis indicated downward trends for annual, winter, spring, and summer values, whereas autumn showed a slight upward trend. In addition, the average magnitude trend per decade was approximately −2.5%, −3.5%, +4.8%, −0.8%, and +3.3% for annual, winter, autumn, spring, and summer seasons, respectively. On the contrary, the drought trend and the associated magnitude per decade for the Taxiarchis forest were found to be as follows: annual (+2.2%), winter (+6.2%), autumn (+9.2%), spring (+1.0%), and summer (−5.0%). The performed statistical test showed that the reported trend was statistically insignificant at a 5% significance level. These results may be a useful tool as a forest management practice and can enhance the adaptation and resilience of forest ecosystems to climate change.