This study examined the cultural identity and cultural connectedness of multiple generations of American Indians whose families had been living continuously in an urban area for 40 to 50 years. The intent of the current study was to better understand how members of this group developed and maintained their cultural identities while living away from a tribal community and as a small percentage of the population of a large and culturally diverse metropolitan area. The study also sought to identify what constituted cultural connectedness–a term used frequently amongst urban Indians that appears to encompass factors of importance to being American Indian. Three or four generations of members from five families were interviewed to explore not only the development and maintenance of cultural identity and connectedness, but of equal importance, how these phenomena may be evolving over the course of multiple generations and are impacted by urban living. A phenomenological approach was utilized to capture the lived experiences of study participants, and interviews were analyzed using Giorgi’s methodology for the phenomenological reduction of qualitative data. Findings revealed meaning structures (what constituted the phenomena) and styles (how the phenomena were exhibited) of cultural identity and cultural connectedness, including the cognitive, affective, and behavioral constituents of each of these phenomena. Implications for social work research, education, and practice were discussed. The new knowledge generated by this study may help agencies and those working with urban Indians to design and provide services that are more culturally relevant, as well as assist practitioners in their efforts to be better informed and skilled at working with this population.