The timing of spring leaf development, trajectories of summer leaf area, and the timing of autumn senescence have profound impacts to the water, carbon, and energy balance of ecosystems, and are likely influenced by global climate change. Limited field-based and remote-sensing observations have suggested complex spatial patterns related to geographic features that influence climate. However, much of this variability occurs at spatial scales that inhibit a detailed understanding of even the dominant drivers. Recognizing these limitations, we used nonlinear inverse modeling of medium-resolution remote sensing data, organized by day of year, to explore the influence of climate-related landscape factors on the timing of spring and autumn leaf-area trajectories in mid-Atlantic, USA forests. We also examined the extent to which declining summer greenness (greendown) degrades the precision and accuracy of observations of autumn offset of greenness. Of the dominant drivers of landscape phenology, elevation was the strongest, explaining up to 70% of the spatial variation in the onset of greenness. Urban land cover was second in importance, influencing spring onset and autumn offset to a distance of 32 km from large cities. Distance to tidal water also influenced phenological timing, but only within ~5 km of shorelines. Additionally, we observed that (i) growing season length unexpectedly increases with increasing elevation at elevations below 275 m; (ii) along gradients in urban land cover, timing of autumn offset has a stronger effect on growing season length than does timing of spring onset; and (iii) summer greendown introduces bias and uncertainty into observations of the autumn offset of greenness. These results demonstrate the power of medium grain analyses of landscape-scale phenology for understanding environmental controls on growing season length, and predicting how these might be affected by climate change.