The cultivation of agroforestry systems is regarded as an effective strategy to synergistically mitigate and adapt to climate change in the face of an increased occurrence of regional extreme weather events. This study addresses the question if and under what conditions farmers are likely to adopt agroforestry and wood-based land-use systems in response to regional weather extremes. We conducted a discrete choice experiment to elicit farmers preferences for - and willingness to adopt - agroforestry and wood-based land use systems and combined the results with geo-spatial weather data. Assuming adaptive weather expectations, we regionally simulate land users' dynamic response to extreme weather years in terms of adoption probabilities. We find that farmers in our case study region in Southeast Germany have a negative preference for alley cropping and short rotation coppice compared to an exclusively crop-based land use system. However, the results from the simulation of a 2018-like extreme weather year show that alley-cropping systems (i.e. agroforestry) might have a very high probability of being adopted in the medium to long-run under different scenarios, thus enhancing farmers' resilience to climate change.