As with the broad field of deep learning, autonomy is a research topic that has experienced a heavy explosion in attention from both the scientific and commercial industries due to its potential for the advancement of humanity in many cross-cutting disciplines. Recent advancements in computer vision-based autonomy has highlighted the potential for the realization of increasingly sophisticated autonomous ground vehicles for both commercial and non-traditional applications, such as grocery delivery. Part of the success of these technologies has been a boon in the abundance of training data that is available for training the autonomous behaviors associated with their autonomy software. These data abundance advantage is quickly diminished when an application moves from structured environments, i.e., well-defined city road networks, highways, street signage, etc., into unstructured environments, i.e., cross-country, off-road, non-traditional terrains. Herein, we aim to present insights, from a dataset perspective, into how the scientific community can begin to expand autonomy into unstructured environments, while highlighting some of the key challenges that are presented with such a dynamic and ever-changing environment. Finally, a foundation is laid for the creation of a robust off-road dataset being developed by the Engineer Research and Development Center and Mississippi State University’s Center for Advanced Vehicular Systems.