Recent sustainability agendas come with the dual mission of responding to climate change and the loss of biodiversity. One strong trend is the increase in the number of trees in urban environments, initiatives often agglomerated under the label of urban forestry. The main focus of this article is to contribute to the development of this discourse by exploring the designerly aspects of urban forestry. This is done by unpacking the concept of ‘urban forestscapes’ as a dynamic and relational concept, derived from a landscape perspective that opens up to spatio-temporal, synthetic, and trans-scalar approaches, and further developed through a process of embedding the research both in relation to literature and in situ. Two wooded areas are studied at the Alnarp campus of the Swedish University of Agricultural Sciences (SLU), in the Malmö- Copenhagen conurbation. The campus holds the first landscape laboratory in Scandinavia, a real-world experimentation site dedicated to the study of urban forestry and woods. The article suggests a recognition of the interpretative openness of the concept in addition to its hybrid qualities with the synthesizing power of overcoming divisions like that of nature/culture or forest/city. The results include insights into experiential characteristics of urban forestscapes as well as methodological considerations.