The Cavalier opened in 1927, deriving its name from a contest held in a local newspaper. The original Colonial-style hilltop structure overlooked the beach and catered to a well-to-do clientele, who arrived by Pullman car to the Cavalier’s own rail stop. When the Cavalier golf course was completed later that year it covered 6,060 yards, with some holes modeled after the famous North Berwick and St. Andrews in Scotland and Chicago??s golf club at Fox Chapel. A beautiful sunken garden was planted on the south side. Its flowers were used to decorate each guest room, as well as the dining room and lobby. In all, the Cavalier originally consisted of 195 guest rooms and 350 acres (290 acres of golf course and 60 acres of hotel property).
On Memorial Day in 1929, the Cavalier Beach Club opened for the first time to the music of the McFarland Twins, the former saxophonists of the Fred Waring Orchestra. The club was the forerunner of all beach clubs, and none of those that followed ever overtook it or even kept pace with it. For the next three decades, the Cavalier was the largest employer of big bands in the world. Every major big band of the time played here, including Sammy Kaye, Les Brown, Benny Goodman, Vaughn Monroe, Cab Calloway, Harry James, Jimmy Dorsey, Woody Herman, Artie Shaw, Lawrence Welk and Glen Miller.
During World War II the U.S. Navy used the hotel as a radar training school, herding sailors into cleaned out stables and conducting classes in the drained swimming pool. Cavalier Oceanfront opened in 1973, and it was decided the original Cavalier, renamed Cavalier on the Hill, would be closed. Cavalier Oceanfront was built 11 stories high. Due to popular demand, however the Cavalier on the Hill reopened five years later. In 2002 the Cavalier completed a multi-million dollar restoration. The Cavalier of today consists of two hotels: the original, Cavalier on the Hill, and Cavalier Oceanfront, with a total of 400 guest rooms.