The article is demonstrates the differentiation of the intensity and characteristics of entrepreneurial activities in Belarus. With respect to many features, Belarus seems to be divided into the western and eastern part, that is, between the territory belonging before World War II to Poland and USSR. The eastern part is more urbanized (76% of urban population comparing to 60% in the west), includes largest cities and has better education indicators that the western part. As the entrepreneurship is highly correlated with education level and the degree of urbanization, it is not surprising that small business is most intense in Minsk and eastern Belarus. However, of the areas characterized by similar urbanization and education level, but located at different sides of the pre-war border, the entrepreneurship is decidedly more developed in the west. The research was conducted in the two regions: Grodziensk (western Belarus) and Witebsk (eastern Bealrus). It showed that the entrepreneurs from the western part of the republic are more free market oriented. While they main request from the central government was simply: less regulations, their counterparts in the east demanded rather more direct support from the state. This difference is the legacy of historical divisions and closer links of the western Belarus with the market economies of Poland and Lithuania.