The visual system continuously adjusts its sensitivities to various visual features so as to optimize neural processing, a phenomenon known as adaptation. Although this rapid form of plasticity has been extensively studied across numerous sensory modalities, it remains unclear if its dynamics can change with experience. Specifically, the world we live in is composed of many different environments, or contexts, each of which contains its own statistical regularities. For example, forests contain more vertical energy and greenish hues than a desert landscape. Here we investigated the possibility that through experience, the visual system can learn statistical regularities in the visual input, and use this knowledge to adapt more quickly. In two sets of experiments, participants repeatedly adapted to previously unexperienced regularities in orientation statistics over the course of 3-4 sessions. They adapted either to rapidly presented sequences of oriented gratings containing orientation biases, or to natural visual input that was filtered to alter its orientation statistics. We found that experience did increase adaptation rate, but only in the experiments where participants adapted to a single set of altered statistics of natural input. We found no changes in adaptation rate in experiments where participants periodically switched between adapting to different statistical regularities. These results demonstrate that adaptation and experience can interact under some circumstances.