The article is interested in the ways that Estonia’s self-perception changed in relation to Europe over the Soviet years and during the re-establishment of the independent state. More specifically, the focus is on co-articulating the “Soviet question” in relation to the “European question”: in what ways did the decades of Soviet rule impact the understanding of Europe and Europeanness in Estonian national imaginaries? In such an analysis, many different factors have to be taken into account: the understanding of Europeanness before the Soviet era; the matter of the Soviet colonial matrix of power; changes within the USSR over the decades in question; the long-rooted orientalization of Eastern Europe in West-European imaginaries, the role of Soviet state-promoted ideologies on local cultural imaginaries. In order to address this complex set of problems, it is useful to proceed from a multi-scalar understanding of social phenomena. From this perspective, Estonia’s geopolitical “relocation” from the Soviet West to the European East, during the re-establishment of the Estonian republic, can be articulated as a shift in the geopolitical scale-system. In more general terms, attention to scale as a “tool for bounding space at different geographical resolutions” enables us to perceive historical conditions as complexly multiscalar. A multiscalar approach reveals how meaning-making unfolds through interaction across different scales of sociopolitical realities and imaginaries, and how in the Soviet-era Estonian SSR, local, regional, and global scales formed complex and dynamic systems of inter-dependency. Keywords: Cultural imaginaries, multiscalarity; Soviet colonial rule; aesthetics of Europeanness; imaginary geographies