The COVID-19 pandemic created an enormous disruption to the everyday life of the modern society. Among the various urban systems, transportation services were among those that suffered the most significant impacts, particularly severe in the case of highways. This paper addresses the challenges and responses to the pandemic from a private highway operator’s perspective and from a multidisciplinary perspective. Highway operators faced two main challenges: on one hand, the need to cope with the potential disruption caused by the pandemic and a national lockdown for almost three months, the provision of road services, and the requirement to ensure the proper operation and maintenance, and on the other hand, the strong negative impact of the pandemic on levels of traffic. Our case study shows that the operator’s management response in question is essentially characterised by being a first response to short term impacts while balancing for workers health and safety, engineering and management, internal business management, and overall economic impact. Highway operators were hardly prepared for such an event and became more focused on prioritising their employees and clients’ safety to avoid service disruption. Regarding levels of traffic, the pandemic has had severe effects, although to a varying degree, depending on the different types of vehicles (heavy, light, passenger, freight, among other types of vehicles) and the location of highways (coastal vs. interior). The lessons learnt can be valuable in future disruptive events and for other highway concession operators.