Current trends in the development of the economy require a radical transformation of the transport infrastructure of Russia within the framework of the concept of Industry 4.0. Important parameters of development are the achievement of cost-effectiveness, digitalization, safety, scalability and environmental friendliness of transportation. Advanced directions are the creation of infrastructure for scaling electric and autonomous vehicles that is integrated into a single virtual platform, thereby forming a single cybernetic system. There is the dynamics of the efficiency indicators of freight and passenger transportation in the chapter. The correlation and regression model of digital activity of transport complex enterprises is created. A logical and information model of the development of the transport system in the context of digitalization is proposed. The results of the study can be used for strategic planning of the development of transport infrastructure in Russia.