The Cavalier Virginia Beach, Autograph Collection

The Cavalier opened in 1927, deriving its name from a contest held in a local newspaper. The original Neo-Classical 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 guestroom, as well as the dining room and lobby. In all, The Cavalier originally consisted of 195 guestrooms 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 that followed ever overtook 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. Ten U.S. presidents have stayed at The Cavalier, and some of the countless other famous guests include: F. Scott Fitzgerald, Judy Garland, Will Rogers, Bette Davis, Jean Harlow, Mary Pickford, Betty Grable, and the infamous Fatty Arbuckle. Hank Ketchum drew several "Dennis the Menace" cartoons based upon his family's stay at The Cavalier.

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. The 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 the new millennium consisted of two hotels: the original Cavalier on the Hill, and Cavalier Oceanfront, with a total of 400 guestrooms.

In 2014, all structures on the 22-acres of land were closed, and in the time since, The Cavalier Oceanfront and Beach Club was demolished to begin making way for the next generation of Virginia Beach guests. The near 100-year old Cavalier on the Hill was placed on the National Register of Historic Places, already having made Virginia Landmark status.

In 2018, following an $85 million restoration, the property reclaimed its original name of The Cavalier and re-opened as a member of Marriott’s esteemed Autograph Collection. The painstaking remodel brought new life to many of the original Neo-Classical features that made The Cavalier a visual oceanfront icon. Exterior details, like the pedestals and finials, the iconic-style pilasters and the portico with Classical columns, have been meticulously and respectfully restored. Much effort went into salvaging each of the original windows on the first floor and in public spaces, which required several hundred man hours with most of the work completed by hand. Inside, much of the original paneling, plaster ornamentation, terrazzo flooring, and painted ceilings were also thoughtfully reconditioned to historical accuracy. The interior can be described as inspired by the era, with an elegant, modern twist. It features grand chandeliers, original mirrors, and a warm color palette with a pop of color. There are also popular textures of the original era like rich velvets, vibrant art, as well as marble baths that are just as luxurious and spa-like for the modern traveler as they were for the first hotel guests in 1927.

The Cavalier Virginia Beach, Autograph Collection, a member of Historic Hotels of America since 2003, dates back to 1927.