This paper is an empirical examination of the relationship of the physical, land-use, and social characteristics of the environment at the microscale to people’s behavior and perceptions toward walking. Using the data from surveys and interviews, this research emphasizes the integration of user perceptions and subjective measures to understand the impact of environmental characteristics on walking behavior on Main Streets. Building-level factors include interesting and engaging storefronts, signage and displays, articulated building facades, variety and range of businesses, and uniqueness of goods and services.