The Florida Land Boom of the 1920s left its mark on St. Augustine with the residential development (though not completion) of Davis Shores, a landfill project on the marshy north end of Anastasia Island. It was promoted as "America's Foremost Watering Place". It was reached from downtown St. Augustine by the Bridge of Lions, billed as "The Most Beautiful Bridge in Dixie".
During World War II, St. Augustine hotels were used as sites for training Coast Guardsmen, including the celebrated artist Jacob Lawrence and actor Buddy Ebsen. It was a popular place for R&R for soldiers from nearby Camp Blanding, including Andy Rooney and Sloan Wilson. Wilson later wrote the novel The Man in the Gray Flannel Suit, which became a classic of the 1950s.
St. Augustine was among the pivotal sites of the Civil Rights Movement in 1963–1964.
Nearly a decade after the Supreme Court ruling in Brown v. Board of Education that segregation of schools was unconstitutional, African Americans were still trying to get the city to integrate the public schools. They were also trying to integrate public accommodations, such as lunch counters, and were met with arrests and Ku Klux Klan violence. The police arrested
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