Walking infrastructure accessibility is key to providing access to transit systems. This is especially important in disadvantaged communities, known in Massachusetts as environmental justice communities, as these communities are often the most transit dependent. Little research has been done examining the condition of walking infrastructure and its accessibility, and its relationship to transit access. While studies have been conducted in large metropolitan areas around the United States on overall transit access and equity, smaller metropolitan areas have long been overlooked. This research aims to fill the gap in research of walking infrastructure accessibility to transit systems in the context of the Pioneer Valley, Massachusetts (the Springfield, Massachusetts metropolitan area). The Pioneer Valley is composed of the mid-sized city of Springfield as well as smaller surrounding urban, suburban, and rural areas. The focus of this research is to connect the accessibility of walking infrastructure to the accessibility of public transportation. In addition, it aims to create a methodology for examining infrastructure accessibility and condition, allowing for the scoring and evaluation of infrastructure to identify barriers to access and areas in need of improvement. The study does this through the creation of a sidewalk condition and connectivity evaluation matrix, based on existing accessibility literature. This iii methodology was then applied to three small study areas of varying characteristics within the Pioneer Valley. Each of the three study areas has been identified as an environmental justice community. The results of this thesis include an evaluation matrix which can be applied to a variety of study areas as well as field-verified inventories of sidewalk connectivity and condition in the three study areas. A detailed analysis of the resulting inventories identified common accessibility barriers across the study areas as well as trends in accessibility across varied land uses, population densities, and ridership trends.