Plant phenology is a sensitive indicator of the effects of global change on terrestrial ecosystems and controls the timing of key ecosystem functions including photosynthesis and transpiration. Aerial drone imagery and photogrammetric techniques promise to advance the study of phenology by enabling the creation of distortion-free orthomosaics of plant canopies at the landscape scale, but with branch-level image resolution. The main goal of this study is to determine the leaf life cycle events corresponding to phenological metrics derived from automated analyses based on color indices calculated from drone imagery. For an oak-dominated, temperate deciduous forest in the northeastern USA, we find that plant area index (PAI) correlates with a canopy greenness index during spring green-up, and a canopy redness index during autumn senescence. Additionally, greenness and redness metrics are significantly correlated with the timing of budburst and leaf expansion on individual trees in spring. However, we note that the specific color index for individual trees must be carefully chosen if new foliage in spring appears red, rather than green—which we observed for some oak trees. In autumn, both decreasing greenness and increasing redness correlate with leaf senescence. Maximum redness indicates the beginning of leaf fall, and the progression of leaf fall correlates with decreasing redness. We also find that cooler air temperature microclimates near a forest edge bordering a wetland advance the onset of senescence. These results demonstrate the use of drones for characterizing the organismic-level variability of phenology in a forested landscape and advance our understanding of which phenophase transitions correspond to color-based metrics derived from digital image analysis.