Unique data from a 100-m meteorological mast located on the windward side of the Dinaric Alps, Croatia, are compared to high-resolution Weather Research and Forecasting (WRF) model simulations. This was performed for an especially strong and long-lasting (more than 20 days) wintertime bora event. The agreement between the measurements on the mast and the respectiveWRF simulation was generally very good, even with respect to the time series of the turbulence kinetic energy. Based on this finding, which validates the WRF model suitability for numerical simulations of transient winds in windward areas, this approach can be used in future studies to explore the severe bora upwind of the coastal mountains, which has been studied inadequately thus far. In this context, some of the preliminary results are outlined here.