In understanding the relationship between built environments and active living, research has focused on objective physical features of the built environment such as transportation infrastructure and density. However, a focus on the objective features does not adequately consider how a person’s experience or perceptions of these features also influence pursuit of walking as a form of active living. The goals of this article are: 1) to develop an instrument to measure Design Quality Indicators (DQIs) of walking infrastructure in the built environment; and 2) to examine how design quality of this infrastructure relates to its walkability. Using information gathered from a literature review, expert panel feedback, and focus groups, we develop a multi-item Design Quality Indicator (DQI) survey protocol to measure design quality of features associated with walking. DQI ratings of walking infrastructure are compared with an infrastructure measure of walkability in 30 small towns. Findings indicate that design quality can vary within and across infrastructure that is rated as having high walkability. Use of the DQI in association with infrastructure measures of walkability provides a more nuanced understanding of how the built environment impacts active living, as measured by walkability.