The paper will approach the interpretation of the built environment by connecting analytical frames developed in the fields of semiotics and cultural geography. It will focus on specific components of the built environment: monuments and memorials, because it is easily recognisable and publicised that they are built forms erected to promote specific meanings in the public space. The aim of this study is to understand how monuments and memorials convey meanings and how they are variously interpreted at societal levels. Monuments usually embody contradictory, complex and open meanings and thus they cannot be analysed using mutually exclusive categories. Rather, their interpretation unfolds in a myriad of signifying trajectories. There are two main narrative trajectories when approaching the interpretations of the built environment and monuments and memorials specifically: that of the designers, i.e. the wide set of actors that have the mandate to design and erect monuments, and that of the users, i.e. those who use monuments during the course of the everyday life through a myriad of different practices: commemoration and mourning, sightseeing, learning as well as (in)attentive crossing or resistant political practices. Previous research is divided between those concentrating on the interpretations of monuments as intended by their designers and those emphasising their individual and social interpretations. But like the interpretation of texts, the interpretation of monuments lies in an intermediate position between these two poles, i.e., between the designers’ and the users’ interpretations. This paper proposes a model for the interpretations of monuments and memorials that conceives the interplay between designers and users. An interdisciplinary perspective connecting semiotics and cultural geography will be used to explain what strategies designers use to create patterns of interpretation and to show how these strategies are interpreted at societal levels. These ideas are analysed through case studies looking at the multiple interpretations of monuments and memorials in post-Soviet countries in Eastern Europe, with a focus on Estonia. Elites in post-Soviet countries have often used monuments to convey the kinds of meanings they want citizens to strive towards. However, citizens differently interpret monuments in ways elites might have never envisioned. In Estonia, the controversies over the relocation and removal of Soviet monuments has often created political divisions and resulted in civil disorder. While analysing this case study, this paper also contributes to the knowledge of political, social and cultural dynamics in Estonia and in post-Soviet countries in Eastern Europe.