The characteristics of gravity waves excited by the complex terrain of the central Alps during the intensive observational period (IOP) 8 of the Mesoscale Alpine Programme (MAP) is studied through the analysis of aircraft in situ measurements, GPS dropsondes, radiosondes, airborne lidar data, and numerical simulations. Mountain wave breaking occurred over the central Alps on 21 October 1999, associated with wind shear, wind turning, and a critical level with Richardson number less than unity just above the flight level (ϳ5.7 km) of the research aircraft NCAR Electra. The Electra flew two repeated transverses across the Ö tztaler Alpen, during which localized turbulence was sampled. The observed maximum vertical motion was 9 m s Ϫ1 , corresponding to a turbulent kinetic energy (TKE) maximum of 10.5 m 2 s Ϫ2. Spectrum analysis indicates an inertia subrange up to 5-km wavelength and multiple energy-containing spikes corresponding to a wide range of wavelengths. Manual analysis of GPS dropsonde data indicates the presence of strong flow descent and a downslope windstorm over the lee slope of the Ö tztaler Alpen. Farther downstream, a transition occurs across a deep hydraulic jump associated with the ascent of isentropes and local wind reversal. During the first transverse, the turbulent region is convectively unstable as indicated by a positive sensible heat flux within the turbulent portion of the segment. The TKE derived from the flight-level data indicates multiple narrow spikes, which match the patterns shown in the diagnosed buoyancy production rate of TKE. The turbulence is nonisotropic with the major TKE contribution from the-wind component. The convectively unstable zone is advected downstream during the second transverse and the turbulence becomes much stronger and more isotropic. The downslope windstorm, flow descent, and transition to turbulence through a hydraulic jump are captured by a real-data Coupled Ocean-Atmosphere Mesoscale Predition System (COAMPS) simulation. Several idealized simulations are performed motivated by the observations of multiscale waves forced by the complex terrain underneath. The simulations indicate that multiscale terrain promotes wave breaking, increases mountain drag, and enhances the downslope winds and TKE generation.