Once known as Thompson's Amusement Park, Rockaways' Playland was owned by LeMarcus Thompson, until his death. Thompson invented the the modern roller coaster which debuted in nearby Coney Island.

In the early 1900s, the Rockaways were first settled as a summer retreat for Manhattanites. Grand hotels, homes, and amusement parks lined the beach and boardwalk. By the 1930s, the hotels and large homes catering to summer visitors were replaced by smaller bungalows and cottages occupied year-round. Changing tastes and new vacation opportunities after World War II diminished the Rockaways' role as a resort destination and hastened the area's transformation into a more permanent community of year-round residents. The arrival of subway service in the 1950s brought an economically and racially diverse mix of residents to the peninsula.