Sustainability and livability in transportation, as the concepts referring to the capability of transportation systems to maintain the well being of our society, have been widely accepted as the critical principles to improve quality of life and health of communities. The research developed a GIS-based performance measurement system for assessing the roles of transportation in achieving these goals. Using the City of Buffalo, New York as the case study, we collected various data and generated twenty sustainability and livability related performance measures (PMs), including the transportation attributes, land use measures, living condition indicators, and system-wide indices. The analysis on PMs derives several policy implications and suggestions. Lessons and challenges learnt from the PM development process were also summarized to help other relevant initiatives. The PMs, supporting database, case study and findings produced by the research are expected to help a wide range of audience such as policy makers, planners and transportation engineers to gain insights about the sustainability and livability oriented performance measurement.