Inductive thermography is a non-destructive testing method, whereby the specimen is slightly heated with a short heating pulse (0.1–1 s) and the temperature change on the surface is recorded with an infrared (IR) camera. Eddy current is induced by means of high frequency (HF) magnetic field in the surface ‘skin’ of the specimen. Since surface cracks disturb the eddy current distribution and the heat diffusion, they become visible in the IR images. Head checks and squats are specific types of damage in railway rails related to rolling contact fatigue (RCF). Inductive thermography can be excellently used to detect head checks and squats on rails, and the method is also applicable for characterizing individual cracks as well as crack networks. Several rail pieces with head checks, with artificial electrical discharge-machining (EDM)-cuts and with a squat defect were inspected using inductive thermography. Aiming towards rail inspection of the track, 1 m long rail pieces were inspected in two different ways: first via a ‘stop-and-go’ technique, through which their subsequent images are merged together into a panorama image, and secondly via scanning during a continuous movement of the rail. The advantages and disadvantages of both methods are compared and analyzed. Special image processing tools were developed to automatically fully characterize the rail defects (average crack angle, distance between cracks and average crack length) in the recorded IR images. Additionally, finite element simulations were used to investigate the effect of the measurement setup and of the crack parameters, in order to optimize the experiments.