The article studies the influence of the transport infrastructure and the degree of its development on specifics and problems of entrepreneurial activity in a region (case study: Pskov region). The results have shown that the insufficiently high quality of  the transport infrastructure, as well as problems in the area as a whole, including the problem of financing, impede the development of entrepreneurship both in the transport sector and in other areas of business. In the article the authors also present the problems of the transport infrastructure development, assessment of possible ways to solve them. The results and conclusions which are presented in this article could be useful for research of such problems in many other regions of the Russian Federation.