Gentrification has dramatically changed the urban landscape of Washington, D.C. Non-profit alternative jazz venues have become important sites for negotiating this complex process that is re-shaping the city. Each such venue aligns itself with one of the two primary factions of gentrification: new urban migrants or long-term residents. Westminster Presbyterian Church’s Jazz Night in Southwest fosters a community of repeat-attendees resisting social displacement. The Jazz and Cultural Society unabashedly foregrounds ties to long-term residents in highlighting a black identity and its local interconnectedness. CapitolBop’s Jazz Loft demonstrates the difficulties that come with trying to cater to a young audience, and at the same time, resist gentrification. These venues present three perspectives on gentrification and together bring light to the overlapping complexity of gentrification.