Road networks are among the most essential components of a country’s infrastructure. By facilitating the movement and exchange of goods, people, and ideas, they support economic and cultural activity both within and across borders. Up- to-date mapping of the the geographical distribution of roads and their quality is essential in high- impact applications ranging from land use planning to wilderness conservation. Mapping presents a particularly pressing challenge in developing countries, where documentation is poor and disproportionate amounts of road construction are expected to occur in the coming decades. We present a new crowd-sourced approach capable of assessing road quality and identify key challenges and opportunities in the transferability of deep learning based methods across domains.