The present work aims to evaluate the tool wear during the milling process of locomotives wheels—class C. A digital microscope is used to identify both the wear and the damage. The wear or damage, when propagated, can compromise the wheel roughness, which has a significant economic importance to railroad maintenance. A system for image capture composed of an ISM-PM200S INSIZE Digital Microscope and the ISM-Pro software is used to measure the flank wear. Firstly, milling process is applied with different numbers of passes. The results showed that, after flank wear, the most common wear is the thermal crack. It is also possible to observe the appearance of chipping and fracture as a consequence of the combination of thermal and mechanical cracks in the same insert. The inserts are more damaged in the raceway, due to the hardening of this region during its use. Inserts in the frieze region also showed higher values of wear, justified by the conditions of the railway. The highest values observed are around 0.1 mm. It is possible to notice that some inserts showed other damages, such as breaks and chipping, even before reaching the end of life due to wear.