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Dominant narratives about Boston tend to center its history as a stronghold of European immigrant groups, and a place where white supremacy and racial hostility are endemic to the city’s culture. Many Bostonians know that, in reality, it is a diverse city where people of color now make up the majority, yet the trope of Boston as a “white city” remains a powerful one. For people of color in the U.S., cultural festivals have historically created spaces of welcome and provide vital reprieve from daily life that is often textured by white social norms and cultural expression. Gathering in celebration has long been part of the Black liberatory tradition in this country. Scholars in fields ranging from sociology to history have documented the political, economic, and social function of collective Black cultural and artistic expression. From “second line” brass parades to block parties and family reunions, festivalscapes operate as important sites of placemaking through the collective expression of emotion, artistry, and agency. Informed by research on topics ranging from social movements to the arts, this paper draws upon 46 structured observations and 107 on-site interviews with attendees at two Black cultural festivals held in Boston during the summer of 2024. Our analysis revealed that attendees felt as though these citywide events created spaces where they could: (1) be their authentic selves; (2) cultivate Black joy and optimism; (3) develop social connections with others who share a vision of Boston as a center for Black culture; and (4) strategize ways to build a more inclusive city, state, and nation. Our findings highlight the radical potential of cultural and arts events in contemporary challenges to resurgences in white supremacy and cultural normativity in Boston, and beyond.