This article addresses the recent proliferation of small‐scale trading in East Europe with a special emphasis on the profits and perils associated with border‐crossing. The political, economic and symbolic aspects of state borders have changed significantly since 1989, and the economic opportunities associated with border‐crossing as ‘trader‐tourists’ represent one of the major challenges to varying categories of the populations to engage in activities associated with the capitalistic spirit of the new era. With ethnographic material from Varna on the Bulgarian Black Sea coast and some comparative glimpses of Russian street trading in Northern Norway, the article discusses how the border, in representing opportunities as well as risks, regulates the relationship between ethnic categories taking part in the trade as well as that between the controllers and the citizens.