The powered wheelchair (PW) has become an essential mobility assistive technology for people with motor disabilities. A critical step involved in maximizing the end-user experience is evaluating individual functional abilities. Using powered wheelchair simulation for driving analysis offers flexibility for safely evaluating the individual’s driving performance in a variable environment and situations ranging in difficulty. Additionally, it makes it possible to measure numerous variables involved in the driving process. The main objectives of this pilot study were to assess PW users’ outdoor driving abilities to study how the simulator can improve outdoor driving task performance, and to define new objective criteria for evaluating the overall driving process. The study presented involved a group of 12 children and young adults diagnosed with cerebral palsy. Simulations were conducted using ViEW (Virtual Electrical Wheelchair), a 3D wheelchair simulator designed in our laboratory. A customized virtual environment was designed to immerse the user in a life-like driving experience. We used the data collected on the simulator to define driving skills indicators. The acquired skills during simulations were transferable to on-road wheelchair driving. The participants’ performance indicators produced positive results. Computed performance indicators can be a valuable decision-making tool for occupational therapists.