The paper deals with the situation of entrepreneurship in three rural cross-border regions of Lithuania bordering on Kaliningrad Region and Poland, i.e. with Jurbarkas, Šilutė, and Vilkaviškis districts. The entrepreneurship factors in rural areas have been summarised, the outcomes of the research in the entrepreneurship factors of the rural areas of Lithuanian cross-border regions have been presented, and the factors impeding business development in the region have been named. In the contemporary society, the significance of the impact of entrepreneurship in economic, social, and psychological processes of the society development has been increasing. The direction of the society progress and the trajectory of its development is related to its members’ entrepreneurship abilities and opportunities. Individual’s entrepreneurship contributes to the perception and identification of the new opportunities of activity development, thus increasing the social welfare.