There are many types of changes occurring over the Earth's landscapes that can be detected and monitored using Landsat data. Here we focus on monitoring “within-state,” gradual changes in vegetation in contrast with traditional monitoring of “abrupt” land-cover conversions. Gradual changes result from a variety of processes, such as vegetation growth and succession, damage from insects and disease, responses to shifts in climate, and other factors. Despite the prevalence of gradual changes across the landscape, they are largely ignored by the remote sensing community. Gradual changes are best characterized and monitored using time-series analysis, and with the successful launch of Landsat 8 we now have appreciable data continuity that extends the Landsat legacy across the previous 43 years. In this study, we conducted three related analyses: (1) comparison of spectral values acquired by Landsats 7 and 8, separated by eight days, to ensure compatibility for time-series evaluation; (2) tracking of multitemporal signatures for different change processes across Landsat 5, 7, and 8 sensors using anniversary-date imagery; and (3) tracking the same type of processes using all available acquisitions. In this investigation, we found that data representing natural vegetation from Landsats 5, 7, and 8 were comparable and did not indicate a need for major modification prior to use for long-term monitoring. Analyses using anniversary-date imagery can be very effective for assessing long term patterns and trends occurring across the landscape, and are especially good for providing insights regarding trends related to long-term and continuous trends of growth or decline. We found that use of all available data provided a much more comprehensive level of understanding of the trends occurring, providing information about rate, duration, and intra- and inter-annual variability that could not be readily gleaned from the anniversary date analyses. We observed that using all available clear Landsat 5–8 observations with the new Continuous Change Detection and Classification (CCDC) algorithm was very effective for illuminating vegetation trends. There are a number of potential challenges for assessing gradual changes, including atmospheric impacts, algorithm development and visualization of the changes. One of the biggest challenges for studying gradual change will be the lack of appropriate data for validating results and products.