The shrinking glacier atop Kilimanjaro has received much attention as it is one of the few remaining tropical glaciers in the world. Physical drivers ranging from changes in temperature and humidity to shifts in cloud coverage and radiation have been attributed to reducing the ice mass. Studies have utilized varying methods and often use point data sources that tend to be spatially and temporally poor in the region. The objective of this study was to use complementing remote sensing data sets with systematic measurements to delineate ice cap fluctuations and land surface phenology on Kilimanjaro over the past two decades. Multitemporal, fine-scale Landsat imagery (30 m) showed approximately a 70% reduction in ice coverage since 1976. High-frequency (bimonthly) image analysis conducted along a human activity–elevation ecocline showed that the entire mountain, including the subalpine and alpine regions, has undergone an increase in vegetative signal indicating a “greening up” of Kilimanjaro over the past two decades. In addition, upper elevations of Kilimanjaro have undergone a temporal shift, or lengthening, in dry season phenology on the order of one month over the past two decades. The shift in dry season timing is concordant with maximum ablation periods. Overall, this study provides insight into land surface trends at resolutions that are currently lacking in Kilimanjaro climate change analyses.