Flow-like landslides are a dangerous landslide type. They often express gradual movement or seeming dormancy, but occasional reactivation can, in extreme cases, result in catastrophic events. To predict their future behaviour, knowledge of past spatio-temporal development and relationships with hydrometeorological triggers is crucial. Moreover, regional data are more robust than case studies. Dendrogeomorphic (tree-ring-based) methods are a very precise approach for reconstructing past landslide behaviour. Nevertheless, regional reconstructions are very rare, which is probably due to their time-consuming procedures. This paper presents the results of a regional tree-ring-based reconstruction of the spatio-temporal development of flow-like landslides in a selected region in the Outer Western Carpathians. Six selected landslides were studied via analysis of 614 increment cores that came from 307 disturbed trees. The reconstruction provided data for approximately 70 individual landslide reactivation phases that were distributed in 44 event years. Events with regional extension (at least half of the studied landslides were active) were detected in six years (1940, 1941, 1953, 1961, 1985, and 1997). Periods of increased (1950s, 1990s) as well as decreased (1940s, 1970s, 2010s) landslide activity were reconstructed. The use of tree-ring data enabled the construction of landslide probability maps. Based on this analysis, all studied landslides exhibit extremely high probabilities of reactivation during a temporal horizon of 100 years, but even over shorter periods (5 and 20 years), their probability of reactivation is very high. Finally, analysis of meteorological triggers suggests the positive effect of precipitation in May (and possibly in September) to activate landslides with regional extent. Extreme short-duration (1-day) precipitation events probably do not play a role in landslide triggering. Moreover, gradual increases in precipitation totals during periods of at least one-half year preceding the event years were detected.