Drought can be considered a devastating hindrance to the health of not only our natural surroundings, but our everyday lives. It is a costly phenomenon, both in financial and human-life contexts; although mitigation efforts may help, there is no true substitution for actual precipitation. Southern California is no stranger to drought; Ventura County specifically has seen particularly devastating wildfires in the last several years, associated with severe drought periods. In this project we set out to analyze the behavior of variables related to droughts by seeking and combining different sources of information to capture and explain any discernible patterns. We make use of over 50 years of rainfall and streamflow measurements of several water stations provided by the Ventura County Watershed Protection District, as well as weather range data of wind, wind direction, and temperature for Ventura County, provided by the KCMA weather station, and historic Oceanic Nino Index values, provided by the NOAA (National Oceanic and Atmospheric Administration). Our exploratory data analysis findings of this historic data are presented. In particular, we observe that six of the driest years recorded occurred within the last two decades, with the historic low (about 16.5 inches of rainfall per year) happening in the most recent decade. Recognizing the multivariate nature of drought, we also explore potential models involving the different variables present in our data, for descriptive and predictive purposes. Such models can provide a developed understanding of the issue, which could inform decisions aimed at extenuating the effects of drought.