With much of the United State population now choosing to live, work, and recreate in urban locations, cities across the county have begun to look for ways to increase green space to meet the ever-growing demand of residents. One way this has been done is through the integration of urban greenways. Unlike other green spaces, these contemporary corridors are constructed in a manner that they directly traverse both densely populated residential communities and commercial spaces. By being built into the fabric of residential areas, these corridors connect residents who often vary in terms of race, socio-economic status, and culture. While these greenways have been shown to provide traversed communities with numerous benefits, the positive impacts resulting with greenway assimilation may not be equally distributed to communities of color and their residents. Research has shown that in urban settings communities of color and parks located within their boundaries are often avoided by White residents based on preconceived notions of neighborhood crime and disorder. This avoidance results in segregation and social isolation. Additionally, research has shown that the integration of a park or green space into a community of color may represent a threat to neighborhood culture and serve as a catalyst for neighborhood change. However, due to their contemporary nature, the effects of urban greenways on communities of color have been largely understudied and thus in need of additional research. The purpose of this study was to better understand how the integration of Chicago's 606, an urban greenway on the city's northwest side, into the Puerto Rican neighborhood of Humboldt Park was altering the social and structural environments in and around the community. In examining these components, the study highlights and provides insight for city leaders and park officials looking to assimilate similar corridors into their cityscape. This mixed method study included quantitative and qualitative approaches to assess use patterns and the experiences of trail users and neighborhood residents. Findings indicate that urban greenways may present a paradox for the neighborhoods in which they are integrated. The 606 had utility in lowering crime, increasing access for minority residents, and providing a safe space for both active and passive recreation. However, it also demonstrated that stigma associated with minorities and the spaces they occupy, in this case Humboldt Park, had the ability to perpetuate exclusionary practices, resource disparities, and sustain inequities between communities. The study also found that The 606 represented a threat to the Humboldt Park community, providing an entry point for White newcomers and an instrument for developers to accelerate green gentrification. This study fills an existing research gap related to urban greenways and their relationship with urban communities. While the study demonstrated that urban greenways may benefit communities of color, it also showed that these benefits may be inequitable and terse. As the popularity for parks and greenways of this sort increases, more research is needed to better understand the positive and negative impacts on proximate environments.