This study investigates race-related challenges in Oak Park, Illinois, a metropolitan Chicago community nationally known for achieving long-term racial diversity. Since its 1968 Open Housing Ordinance, Oak Park has maintained white residential demand, an achievement elusive to most communities facing racial change. However, despite its racial stability, this study argues that Oak Park faces several racial roadblocks to successful diversity. In-depth interviews with forty Oak Park households, half black, half white, indicate these roadblocks create a color line in which black and white residents experience the community in some fundamentally different ways. The study's findings and recommendations have relevance beyond the Oak Park community. As growing racial and ethnic diversity characterize the 21st century American experience, it is essential that new strides occur in eradicating the residential segregation that persists in many of our nation's metropolitan areas. Communities desiring successful long-term diversity will find the study's unique insights valuable when striving toward this vital national goal.