The significance of play in the construction of landscape involving the feedback relationships between social conventions and the individual and between the individual and physical space, contrastingly, has so far received only little scientific attention. Games, however, take on great significance in the process of socialization in order to introduce the socializing person into the interpretations, valuations, and practices of the social world, which applies correspondingly to landscape. Play is an essential element of comprehending the concept “landscape”. Accordingly, this present essay deals with conceptual considerations of the function of games in relation to the social and individual construction of landscape. The theoretical framing of landscape will be carried out within the theory of the three landscapes, following Karl Popper’s three worlds. This theoretical framing also involves fundamental considerations on the connection between games and landscapes, which will be illustrated in more detail by means of two case examples, i.e., model railroads and pinball landscapes. It is shown that the playful engagement with landscape takes place in two dimensions: On the one hand, role expectations, norms, and values associated with landscape are conveyed, thus providing guidance for individual construction and individual experience of landscape. On the other hand, landscape contingencies can be tested. They address norms of interpretation and evaluation of landscape that are considered as bound together. Moreover, innovations can be tested, which may have been established in the social understanding of landscape.