The present paper reports on a series of studies conducted at the Regional Center for Assistive Technology (Centro Regionale Ausili, CRA) in Bologna, Italy. Our purpose was to identify a set of internationally validated instruments and a training circuit with a view to developing a structured and validated Powered Mobility Device (PMD) assessment and training program. To develop the program, three studies were conducted in order to identify: validated measures for assessing the user’s driving skills and training needs for using a PMD (Study 1); measures for evaluating the outcomes of the PMD (Study 2); and, the elements necessary for building a circuit for conducting PMD training (Study 3). In studies 1 and 2, the Wheelchair Skill Test 4.2 Power Wheelchair (WST) and the Wheelchair Outcome Measure (WhOM) were selected and pilot tested using QUEST 2.0. These studies represent an important step in the development and definition of a PMD assessment and training program to be implemented in routine clinical activities in a regional center for assistive technology in Italy. The measures, the circuit and the program will be further tested in future for validity and reliability in order to assess their efficacy in helping professionals to select the most adequate PMD for users, to conduct specific PMD training, and to evaluate PMD outcomes.