Past practices shape and limit the design imagination of teachers, pupils, parents, governors, and others concerned with designing modern schools. Bringing histories of education to the table in the participatory design process of new school buildings and curricula is necessary. Schools having an extraordinary past have the potential to draw from that prefigurative practice. This paper reports a case study on how the Kees Boeke School in The Netherlands recently has returned to its own history in addressing the needs of its current and future learners in a redesign project. Through addressing the question of how the redesign might reflect a reconnection with the original vision of education espoused by Boeke—learning in relative freedom, with awareness of responsibilities for own and community’s well-being—the school management, architects, teachers, and students took part in a participatory design process. That process and the resulting school design is discussed. From this case study we argue that past adventures in education can inspire current redesign. Past experiences as well as concerns and beliefs about the future are an inevitable influence on initiatives to realise schools for the future, both for schools with experimental and those with traditional histories.