Across Alaska’s Kenai Peninsula, disturbance events have removed large areas of forest over the last half century. Simultaneously, succession and landscape evolution have facilitated forest regrowth and expansion. Detecting forest loss within known pulse disturbance events is often straightforward given that reduction in tree cover is a readily detectable and measurable land-cover change. Land-cover change is more difficult to quantify when disturbance events are unknown, remote, or environmental response is slow in relation to human observation. While disturbance events and related land-cover change are relatively instant, assessing patterns of post-disturbance succession requires long term monitoring. Here, we describe a method for classifying land cover and quantifying land-cover change over time, using Landsat legacy imagery for three historical eras on the western Kenai Peninsula: 1973–2002, 2002–2017, and 1973–2017. Scenes from numerous Landsat sensors, including summer and winter seasons, were acquired between 1973 and 2017 and used to classify vegetation cover using a random forest classifier. Land-cover type was summarized by era and combined to produce a dataset capturing spatially explicit land-cover change at a moderate 30-m resolution. Our results document large-scale forest loss across the study area that can be attributed to known disturbance events including beetle kill and wildfire. Despite numerous and extensive disturbances resulting in forest loss, we estimate that the study area has experienced net forest gain over the duration of our study period due to reforestation within large fire events that predate this study. Transition between forest and graminoid non-forest land cover including wetlands and herbaceous uplands is the most common land-cover change—representing recruitment of a graminoid dominated understory following forest loss and the return of forest canopy given sufficient time post-disturbance.