Alleys evoke powerful images in our collective fear and, yet, play an important role in our American culture. Currently, communities are recognizing the value of the alley to their social landscape and designers and planners are reviving the alley in designs for new communities. What is it about the alley that has communities so excited? Why are alleys being reincorporated into today’s design language? What do alleys contribute to a community’s landscape and how do they contribute to its identity? What do we have to learn about community and urban design from the alley? To answer these questions, this study compares a spectrum of five communities with various types of alleys – Holyoke, Amherst, and Northampton, Massachusetts; New York City; and Kentlands, Maryland. The conclusions drawn from this study indicate that the alley is an expressive landscape in which communities communicate their collective values and ideals and residents negotiate their community’s identity through control, order, and organization, including the naming, maintenance and use of the alley. It is also where boundaries of class, economic status, and affluence are navigated and expressed. Furthermore, the implications of these findings are that urban designers, landscape architects, planners, and engineers must resist the temptation to over-design and micro-manage a place if a truly organic and expressive community is desired. Within this framework, these professionals must also anticipate that a community will change and to allow for its alleys and other spaces to respond to, and reflect, these changes.