Abstract: Comfort is a major requirement in planning pedestrian facilities. Pedestrians walk where they feel comfortable and when they do not feel at ease, they walk elsewhere. A typical example is that filthy, distressed, or too narrow sidewalks induce pedestrians to walk on carriageways. This behaviour jeopardizes road safety and highly dangerous to most users, leave them vulnerable. Unsuitable pavements can be the result of irregular maintenance operations to restore evenness after shock damage, weather phenomena, installation of equipment (e.g., posts, fences, urban furniture) with a reduction of walkable surface, or substandard repair work on pavements and patches due to emergency operations. These problems can be solved with an appropriate maintenance management system, which optimizes financial resources to make smart decisions about how to intervene with an adequate and lasting maintenance operation. This paper defines an evaluation index for sidewalk conditions as a part of an efficient set-up of a Sidewalk Management System, which is similar to the better known Road Management System. The study relies on surveys, as well as the classification and analysis of sidewalk distresses. The authors adapted an index already standardized by ASTM for roads and airports: the Pavement Condition Index (PCI). PCI has been modified to consider the specific types on the sidewalks studied within this paper. To validate the method, a case study of a residential district in Rome, Italy, was carried out. The chosen area lacks regular maintenance and has therefore resulted in a network of unsafe sidewalks. Frequent detour routes were surveyed and related to the level of distresses within a general assessment of safety. This study concentrates on sidewalks with flexible pavements because this type of pavement is the only one adopted in the survey areas and, in general, throughout Italy.