Contemporary climate change in Alaska has caused amplification and unpredictability in disturbance regimes that drive ecosystem function. As a result, many ecosystems across the Boreal and Arctic regions are undergoing abrupt transitions that are recharacterizing landscape patterns, ecological processes, species composition, structure, and trophic biophysical interactions. In this study, I used remote sensing and spatial analyses to classify a dynamic ecosystem in the Caribou Hills Grassland region of Alaska’s Kenai Peninsula, USA. This region is currently undergoing a shift from a historical boreal spruce forest to a savannah-like system as a result of an extensive spruce bark beetle outbreak in the 1990s through the early 2000s that killed thousands of acres of trees, followed by a rapid and intense human-caused fire that burned about 56,000 acres in 2007. To characterize the landcover of the Carious Hills and develop a protocol for monitoring future landcover transitions, I collected two sets of aerial imagery in 2019 and 2021, each collected at a separate spatial resolution and time of year, and used a maximum likelihood classification approach to classify the dominant land cover types (grass, shrub, and spruce). Overall, classification accuracies across both images were above 78%, and I found that the Caribou Hills landscape is currently comprised, on average, of 67% grass, 27% shrub, and 3% spruce. Assessing post-disturbance succession and ecosystem transitions requires long-term monitoring. Because the Caribou Hills Grassland region is large and remote, frequent monitoring through aerial imagery will be valuable for assessing land cover change over time. As the management of shifting ecosystems is relatively new to land managers, approaches such as the one developed in this study can be used as guidance towards innovative monitoring efforts and land stewardship.