The Oregon Trail is an ephemeral artifact of great importance to the history of the United States. While there is a great deal of historical documentation in the way of journals, travel itineraries, and cargo manifests, there is much less documentation in terms of the physical trail itself. That lack of research on the condition of the roadbed, then and now, and of alternate paths taken off the trail are having a deleterious effect on the understanding of this time in history, as the trail itself is disappearing. Using ground-penetrating radar, we have begun digital documentation of the trail and its unique characteristics in a way that has not been widely published. With these new methodologies and the theoretical approach of conflict-event theory, we propose a new process capable of creating a "digital signature" of the Oregon Trail.