In a time of multiple global challenges, trees gain more and more attention as an important component of sustainable land use systems, as they can produce food and provide multiple other ecosystem services at the same time. In Germany, traditional orchard meadows (so-called “Streuobstwiesen”) are in decline, although they are well known for their ecological value. In modern agroforestry systems staple perennial food crops seem to be rarely integrated. Here, we propose to use emerging chestnut cultivation for revitalizing traditional orchard meadows, diversifying forests, and integrating perennial staple food crops in modern agroforestry systems. In this study, we interviewed 64 chestnut growers in Germany and aimed to (1) explore characteristics of chestnut stands and management; (2) evaluate the main motivations, aims, and challenges of chestnut growers; (3) identify perceived outcomes of chestnut cultivation and measures for upscaling; and (4) analyze differences between groups of chestnut growers. Our results show that most growers aimed to increase tree numbers and foster the spread of chestnut trees as cultural assets. Sustainable food production was the motivation most often named by the respondents. A guide for cultivation, as well as better funding, were mentioned as the most wanted and easy to implement measures for up-scaling production and consumption. Junior chestnut growers were better connected to other chestnut growers and were more motivated by sustainable food production than senior growers. Pest and diseases as well as legal and funding situations were aspects hampering chestnut cultivation. We suggest that chestnut trees can serve as a valuable element of a diverse tree crop landscape providing staple food crops while supporting ecosystem services.