In the twentieth century, New York State’s Catskill Mountain resort area was an “All-American” vacationland. Each summer, many different racial and ethnic minorities sought a brief respite from their lives and labor in New York City at boarding houses, resorts, and bungalows scattered throughout the mountains. Collectively, these groups contributed to the development of a highly segregated resort area that reflected, on an exaggerated scale, the racial, ethnic, and class divisions within New York City and the nation as a whole in the twentieth century. This dissertation examines the Catskills resort landscape through a comparative analysis of African American, Puerto Rican, and Italian summer resorts from 1920 to 1980. It draws on oral history interviews, newspaper accounts, and archival sources to trace the history of these resorts from their origins as modest boarding houses in the 1920s and 1930s, to their immense growth in popularity after World War II, and their decline in the final decades of the twentieth century. All three groups created resorts where they sought to foster and sustain a sense of collective pride and identity in insulated recreational environments, free from the racism and nativism of dominant white society. Summer resorts catered to and were shaped by each group’s distinct social, cultural, and political needs; these needs evolved according to changes in vacationers’ lives in urban and suburban areas around New York City. Considered alongside one another, these histories demonstrate that summer resorts were not solely a stepping-stone for ethnic minorities on their way to assimilation and acceptance in American society. In the decades following World War II, Italians successfully reconfigured the meanings of their ethnic identity to gain acceptance as white Americans. By contrast, racial minorities found that racism continued to hamper their efforts at upward mobility, well after legal barriers to their success were dismantled. Summer resorts built upon and helped naturalize patterns of segregation and inequality that structured vacationers’ everyday lives in the New York metropolitan area. In this sense, too, the resort landscape was “All-American”—a striking reflection of the country’s deeply entrenched racial hierarchy.