Soil moisture dynamics are known to vary highly in space and time, especially given soil-plant-water and human interactions in agricultural environments. In this thesis, soil moisture fluctuations under two agricultural soil conditions – cover cropping and soil compaction – were examined over both seasonal (study 1) and event (study 2) timescales. Study 1 revealed that the activation of lateral soil water flow pathways varied seasonally and across soil conditions. Vertical flow pathway activation varied with soil condition and depth but showed minimal seasonality. In Study 2, soil moisture responses to dry spell events were similar between soil conditions, while soil moisture responses to rainfall events were different between cover-cropped and compacted soils. Given the linkages between soil water and nutrient export, this thesis provides valuable information about short- and medium-term soil water dynamics, which can help guide policy makers and crop advisors in developing region-specific agricultural water and nutrient management strategies.