Alleys are underutilized as contemporary pedestrian thoroughfares because they have historically served to hide the utilitarian functions of urban life. Thus, the narrow spaces fail to provide the necessary amenity required for active pedestrian spaces, and are therefore shrouded by negative stigmas. As a result, alleyways are disregarded as being viable pedestrian thoroughfares and therefore fail to be integrated into existing urban networks. The redevelopment of Roberts Alley in Fargo, North Dakota seeks to evaluate and apply the traditional urban design principles of transparency, complexity, and human scale in order to challenge the historic stigmas and usage patterns surrounding alleyways. By introducing pedestrian amenity, whether physical (seating and lighting) or perceived (comfort and safety), redevelopment strives to promote thoroughfare and engage adjacent commercial business. The resulting design research serves as a site-specific plan for redevelopment, as well as a pedestrian model that can be applied to similar urban alleyways throughout the country.