Drawing Lines: Soviet and Post-Soviet Cultural Representations of Borders in the Pskovian Amateur Art examines how amateur culture activities have been and are used both to assimilate and to differentiate neighbor nationalities. The aim of the study is to locate the cultural changes when a state border starts to be represented as ‘outpost’ of an empire or ‘link’ between neighbor nations in amateur cultural practices. This study continues firstly, my research in the Pskov province, and secondly, my study on how amateur artists’ creative potential is used to convey some politically selected and controlled themes. I seek answers to the following questions: 1) How people are engaged in amateur cultural practices in order to demolish and constitute cultural borders? 2) What kind of discursive practices in amateur art has been used de-construct and re-construct a cultural border in the Pskov province? 3) When does the de-construction and re-construction begin to be seen in amateur cultural activities? This study investigates writing activities in the Pskov province on the Russian–Estonian, Russian-Latvian and Russian-Belarusian borderlands. The studied periods are the post-war (WWII) period (late 1940s–1960s) and the period after the collapse of the Soviet Union (starting from the beginning of 1990s).