This study examines the effects of land-use policies and natural events on the evolution of two wooded pastures in the Jura Mountains in Switzerland between 1934 and 2000. The socioeconomic context and the local conditions were seen as major driving forces influencing land management practices which in turn redefined land-use policies. We studied the dynamics of the Jura Mountains’ wooded pastures, combining a thorough knowledge of the historic context with aerial image analysis. Besides pointing out general milestones in the evolution of Swiss land policy, we compiled chronicles on the management for both study sites on the basis of archives and interviews. Aerial images taken at time intervals of approximately 15 years were chosen to identify land-cover changes. The method used to analyze them relied on a structural classification of phytocoenoses, thus allowing the determination of four categories of tree-cover densities ranging from unwooded pastures to ungrazed forest. We reported overall aerial changes for each tree density class as well as spatial transitions from one category to another. The combination of spatial statistics with qualitative data depicting the evolution of the historic context gives a better understanding of the land-use changes and their rationale. The most important changes in tree density occurred during World War II and resulted in a more open landscape. The intensive use of wooded pastures during the war was the consequence of a high demand for wood and food resources. Postwar protectionist regulations, agricultural subsidies, and technical improvements maintained considerable pressure on wooded pastures. Storms and drought episodes further exacerbated this process in some areas. The trend then reversed from the 1970s onwards because of the limitations put on milk production and the falling price of wood. This resulted in a more extensive use of pastures, leading to tree encroachment. However, remote sites were more impacted than pastures closer to inhabited areas, which exhibited a trend towards more segregation between grassland and densely wooded pastures. With both extensification and segregation of land use, the complex vegetation mosaic and the landscape diversity that characterize wooded pastures are threatened but still offer good economic opportunities that call for differentiated management strategies.