The technical, operational and organizational-economic problems of the engineering and construction design of the Transcontinental Railway crossing the Bering Strait are under consideration. The particularities of the Russian and North American transport systems are noted and ways of reducing existing contradictions are proposed. Examples of similar large-scale investment transport projects in Europe and Asia are given. The history of the idea and the beginning of the progecting of the transition has more than a century. However, global risks and the challenges of some periods of history are constantly pushing back the start of the project. The paper gives a brief overview of the economic and geographical region of economic gravitation the construction of the Transcontinental crossing between Russian Chukotka and American Alaska. On the Russian side, there is a clear lag in the development of transport and economic infrastructure. The institutional problems of design and construction are noted, without the solution of which the further movement of the project is impossible