The application of deep learning, specifically deep convolutional neural networks (DCNNs), to the classification of remotely-sensed imagery of natural landscapes has the potential to greatly assist in the analysis and interpretation of geomorphic processes. However, the general usefulness of deep learning applied to conventional photographic imagery at a landscape scale is, at yet, largely unproven. If DCNN-based image classification is to gain wider application and acceptance within the geoscience community, demonstrable successes need to be coupled with accessible tools to retrain deep neural networks to discriminate landforms and land uses in landscape imagery. Here, we present an efficient approach to train/apply DCNNs with/on sets of photographic images, using a powerful graphical method called a conditional random field (CRF), to generate DCNN training and testing data using minimal manual supervision. We apply the method to several sets of images of natural landscapes, acquired from satellites, aircraft, unmanned aerial vehicles, and fixed camera installations. We synthesize our findings to examine the general effectiveness of transfer learning to landscape-scale image classification. Finally, we show how DCNN predictions on small regions of images might be used in conjunction with a CRF for highly accurate pixel-level classification of images.