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Courtesy Milne Special Collections and Archives Department, University of New Hampshire Library, Durham, New Hampshire.

Hazel and Clayton Sinclair Sr., active in their community’s NAACP, were thrilled by the passage of the 1964 Civil Rights Act, which barred businesses from discrimination on the basis of race. They knew, however, that the act would have negative consequences for their own business. Sure enough, visitorship declined at establishments like Rock Rest and the Cummings’ Guesthouse. There remained a trickle of loyal visitors who returned year after year, but for the most part, black vacationers took advantage of the wider variety of options now available. Rock Rest finally closed in 1976.

Oak Bluffs, due to its vibrant community of landowning African Americans, continued to grow as a vacation community and is still a prominent resort for African Americans. Thanks in large part to summer visits by Presidents Clinton and Obama, Oak Bluffs is more well-known and popular than ever.

Travel was not easy for black Americans in the mid-twentieth century. There was no way to know whether they would be welcomed or turned away at unfamiliar destinations. Nevertheless, middle class African Americans, who had already overcome numerous obstacles, persevered. With determination and creativity, they created a network of places where they could feel at home and enjoy summer in New England.