Wind energy potential in complex terrain is still poorly understood and difficult to quantify. With Switzerland’s current efforts to shift to renewable energy resources, it is now becoming even more crucial to investigate the hidden potential of wind energy. However, the country’s topography makes the assessment very challenging. We present two measurement campaigns at Lukmanier and Les Diablerets, as representative areas of the complex terrain of the Swiss Alps. A general understanding of local wind flow characteristics is achieved by comparing wind speed measurements from a near-surface ultra-sonic anemometer and from light detection and ranging (LiDAR) measurements further aloft. The measurements show how the terrain modifies synoptic wind for example through katabatic flows and effects of local topography. We use an artificial neural network (ANN) to combine the data from the measurement campaign with wind speed measured by weather stations in the surrounding area of the study sites. The ANN approach is validated against a set of LiDAR measurements which were not used for model calibration and also against wind speed measurements from a 25-meter mast, previously installed at Lukmanier. The statistics of the ANN output obtained from multi-year time series of nearby weather stations match accurately the ones of the mast data. However, for the rather short validation periods from the LiDAR, the ANN has difficulties in predicting lowest wind speeds at both sites, and highest wind speeds at Les Diablerets.