The aim of this thesis was to identify the characteristics of path segments and routes that are associated with where older residents choose to walk for recreation or for getting to destinations in retirement communities. The goal was to use the findings from this study to help formulate criteria and strategic choices that can be used to design retirement communities that support walking among elderly residents. Case studies were conducted at three Continuing Care Retirement Communities. The study shows that route choice for walking to destinations is shaped by practical considerations of distance and convenience and largely determined by the relative location of destination and origin. On the other hand, route choice for recreational walking is more complex and is determined by local, relational and structural environmental characteristics of the path segments that comprise the routes as well as characteristics of the residents themselves. Residents chose routes of different difficulty level for walking based on their physical abilities and health. This study also found that many residents chose to walk indoors for recreation, especially along corridors between resident apartments. Understanding how the different factors together shape route choice leads to the clarification of design alternatives. This study suggests that designing campuses to support walking involves not only a careful consideration of individual local path segment characteristics but also an understanding how path segments and routes fit within the larger network of path segments on campus. Further, it is important to design routes with a range of characteristics and a range of challenge so that residents have many options to choose from and they have the option to move from a lower level of challenge to a higher one when they feel ready.