A contextual audio system configured to adjust audio playback in response to positional data. The contextual audio system may include a wearable audio device and, optionally, a sensing device. In some embodiments, the sensing device and the wearable audio device are the same. Generally, the contextual audio system employs different types of data to determine a user's location and/or activity (both of which are examples of “context”) and adjust audio output of the wearable audio device portion of the system.