Orthopedic drilling as a skill demands high levels of dexterity and expertise from the surgeon. It is a basic skill that is required in many orthopedic procedures. Inefficient drilling can be a source of avoidable medical errors that may lead to adverse events. It is hence important to train and evaluate residents in safe environments for this skill. This paper presents a virtual orthopedic drilling simulator that was designed to provide visiohaptic interaction with virtual bones. The simulation provides a realistic basic training environment for orthopedic surgeons. It contains modules to track and analyze movements of surgeons, in order to determine their surgical proficiency. The simulator was tested with senior surgeons, residents and medical students for validation purposes. Through the multi-tiered testing strategy it was shown that the simulator was able to produce a learning effect that transfers to real-world drilling. Further, objective measures of surgical performance were found to be able to differentiate between experts and novices.