The research aims to identify groups of Russian regions that share similar values in factors crucial for developing regional transportation systems and describe the distinctive characteristics of each group. The authors employ comparative and dispersion methods and agglomerative and divisive cluster analysis techniques. Indicators from the Federal State Statistics Service of the Russian Federation (Rosstat) for 2021 and 2022, characterizing socio-economic, infrastructural, and climatic factors affecting the development of regional transportation systems, were selected for clustering. Using Ward’s method, the authors identified and described six clusters: the capital cluster, the cluster of sparsely populated regions leading in per capita GRP, average-performing regions, resource-extracting regions in the North and Asian part of Russia, economically advanced regions, and the “agricultural South.” These clusters were subsequently refined using the k-means method. The scientific novelty of this research lies in the refined clustering of the Russian Federation’s subjects based on a set of factors influencing the development of regional transportation systems. The resulting clustering will be useful in formulating regional and federal programs and initiatives to develop and improve the transportation infrastructure of Russian regions, as well as in setting appropriate priorities and coordinating interregional cooperation.