The cultivation of agroforestry systems is regarded as an effective strategy that can help synergistically mitigate and adapt to the adverse impacts of climate change and regional extreme weather events. This study addresses the question of whether, and under what conditions, farmers are likely to adopt agroforestry systems in response to regional weather extremes and presents a novel research approach to tackle this question. A discrete choice experiment was conducted to elicit farmers’ preferences for agroforestry and wood-based land use systems. The results were combined with geospatial weather information. Assuming adaptive weather expectations, land users’ dynamic responses to extreme weather were simulated in terms of adoption probabilities. Farmers in the case study region in southeastern Germany were found to have a negative preference for alley cropping systems (i.e. agroforestry) 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 event showed that alley cropping has a high probability of being adopted in the long-term. This study provides novel insights into the adaptive uptake of climate-resilient agroforestry systems. This information can be used to develop more effective policies and programs to promote agroforestry as a climate-resilient land-use strategy.