The expansion of road networks, taken place during the last decades, was driven by technological progress and economic growth. The most innovative products of this trend—modern motorways and international road corridors—provide an excellent level of service, traffic safety and necessary information to travelers. However, despite this undeniable progress, major impediments and respective challenges to road authorities and operators still remain. The present paper analytically presents the main current challenges in the road engineering field, namely: a) financing new projects, b) alternative energy resources, especially renewable energy, c) serviceability, including maintenance of road infrastructure, traffic congestion and quality of the network, d) climate change hazards due to greenhouse gas emissions increase, e) environmental impacts, f) safety on roads, streets and motorways, and g) economy and cost-effectiveness. In each country and over each network, challenges and concerns may vary, but, in most cases, competent authorities, engaged in road development policies, have to deal with most of these issues. The optimization of the means to achieve the best results seems to be an enduring stake. In the present paper, the origin and the main features of these challenges are outlined as well as their tendency to get amplified or diminished under the actual evolving economic conditions worldwide, where growth alternates with crisis and social hardship. Moreover, responses, meant to provide solutions to the said challenges, are suggested, including research findings of Aristotle University and innovative technological achievements, to drive the transition to a more sustainable future.