Rich coastal topography and variable synoptic systems contribute to a wide range of weather phenomena along the Northern Gulf of Alaska, including coastally trapped wind and stratus events. Such sudden changes in cloud cover and wind direction may have important impacts on both the marine and aviation communities. On June 9, 2008, a band of easterly winds and stratus propagated along the Gulf of Alaska towards the Kenai Peninsula, but eventually the stratus split and propagated in opposite directions. Available observation data were examined and high-resolution nested grid simulations were run using the University of Wisconsin Nonhydrostatic Modeling System (UWNMS). The relationship of this propagation to other coastally trapped phenomena was evaluated.