This paper reports the initial results of a pilot study investigating the relationships among long-term land use, settlements, historic population, and their potential influence for understanding and evaluating current and future land use. Most of our work to date has been focused on evaluating changing patterns of historic settlement and its relationship to what we know about the historic environment and landscape. Here, we instead rely on remotely-sensed big data as a first step to see how patterns of past land use are correlated with what we know about current land use and land cover. The pilot study initiates a broader research agenda that better incorporates what we know about past landscapes into contemporary land use decisions and to offer critical insights into how the future could be shaped by integrating information about the past. As a first step, the analysis is intentionally broad so that our next steps can provide the fidelity and resolution to offer place based information for design and planning. Nevertheless, it offers a unique window of perception into current land use and a platform for operationalizing evolutionary uses of the past for better managing, designing, and planning complex land systems and moving beyond analogic uses.