Drystone walls are a tangible and eye-catching structural element in the landscape. They bear witness to natural and human action and interaction and integrate the prefiguration of territory with aspects of space, life and agricultural production. How should the landscapes that they create be conserved and maintained in the future—and by whom? How can a territory accommodate considerations of space, nature, geology and material culture? This chapter aims to analyse and identify how landscape observatories can detect novel and relevant data and knowledge, and how the involvement of landscape observatories can be more effective. While there is a growing body of data and mapping, there has been little attention on particular site-specific perspectives, and how to visualise and communicate with the public. To some degree, the feeling of loss obstructs a nuanced and realistic strategy for future magic and attractive drystone landscapes. Based on cases from Småland, Sweden, Britain and Mallorca, and on three heritage cases from Jelling (Denmark), Kalkriese (Germany) and Olot (Spain), I critically analyse and identify a potential model for the future role and involvement of landscape observatories in the elaboration and management of drystone landscapes and suggest selecting particular sites in association with drywalls.