The article is devoted to the study of the features and directions of digital transformation at the regional level in Ukraine. The purpose of the work is to study the concept of digital transformation; assessment of digital technologies in transport; analysis of Smart-city cases; development of measures for the digital transformation of the transport system of Ukraine at the regional level. In the process of research, the authors used dialectical and abstract-logical methods, which revealed the nature of digital transformation and identified its principles. The application of the logical method made it possible to enrich the scientific characteristics of the concept of "digital transformation". On the basis of systemic and synergistic approaches, directions for the implementation of digital technologies in transport were evaluated. Methods of analysis and synthesis were also applied to research the international practice of digitalization of the transport system at the regional level, as well as to develop proposals for the digital transformation of the transport sector in the regions of Ukraine. The concept of digital transformation in work is defined as a process based on a moving from traditional models, involves qualitative changes in business processes or ways of conducting economic activity, as a result of which digital technologies are implemented, which leads to significant socio-economic effects. The work noted that transport and logistics are the industries in which the economic effect of digital transformation is most tangible. The transport system is most receptive to the introduction of such digital technologies as: Internet of Things, unmanned and mobile technologies, identification technologies, blockchain, big data, paperless technologies, drones, robotic systems, artificial intelligence and neural networks. The cases of digital transformation of regions (EU and Canada) and the Smart City project, an integral component of which is transport, were analyzed in order to determine the possibilities of their implementation in Ukraine under martial law. A number of recommendations have been developed to ensure the digitization of the transport system of the regions of Ukraine and the directions for its implementation have been determined.