The load applied by each rolling element on a bearing raceway controls friction, wear and service life. It is possible to infer bearing load from load cells or strain gauges on the shaft or bearing housing. However, this is not always simply and uniquely related to the real load transmitted by rolling elements directly to the raceway. Firstly, the load sharing between rolling elements in the raceway is statically indeterminate, and secondly, in a machine with non-steady loading, the load path is complex and highly transient being subject to the dynamic behaviour of the transmission system. This study describes a method to measure the load transmitted directly by a rolling element to the raceway by using the time of flight (ToF) of a reflected ultrasonic pulse. A piezoelectric sensor was permanently bonded onto the bore surface of the inner raceway of a cylindrical roller bearing. The ToF of an ultrasonic pulse from the sensor to the roller–raceway contact was measured. This ToF depends on the speed of the wave and the thickness of the raceway. The speed of an ultrasonic wave changes with the state of the stress, known as the acoustoelastic effect. The thickness of the material varies when deflection occurs as the contacting surfaces are subjected to load. In addition, the contact stiffness changes the phase of the reflected signal and in simple peak-to-peak measurement, this appears as a change in the ToF. In this work, the Hilbert transform was used to remove this contact dependent phase shift. Experiments have been performed on both a model line contact and a single row cylindrical roller bearing from the planet gear of a wind turbine epicyclic gearbox. The change in ToF under different bearing loads was recorded and used to determine the deflection of the raceway. This was then related to the bearing load using a simple elastic contact model. Measured load from the ultrasonic reflection was compared with the applied bearing load with good agreement. The technique shows promise as an effective method for load monitoring in real-world bearing applications.