When you think of Virginia Beach, you probably think of summer vacations with the family. But did you know about the coastal city’s history as a retreat for Hollywood celebrities, presidents, and the rich and famous? 

A Small Beach Town Embraces The Finer Things


Photo Credit: Matt Long, @landlopers

It all started in the late 19th and early 20th centuries, as Virginia Beach’s local leaders began dreaming up plans for an extravagant waterfront hotel property. Back then, Virginia Beach was considered a popular vacation destination, but most of the guests came from nearby towns, and out-of-state visitors were less common, as interstate travel was expensive and time-consuming. The city’s existing upscale resort, the Princess Anne Hotel, was ravaged by fire in 1907, and the city leaders wanted to replace it with something bigger and better; however, it would take them almost twenty years to make these plans a reality. 

The Historic Cavalier Hotel Opens

A Historic Photo of The Cavalier Hotel in Virginia Beach

Image Courtesy of the Library of Virginia

After two decades of rumors swirling concerning the construction of a world-class beach resort, the Historic Cavalier Hotel was officially completed in 1927, reflecting the prosperity and extravagance of the Roaring Twenties. The hotel utilized design elements from notable Virginia sites; the ornate plaster columns that flanked the entryway were inspired by Thomas Jefferson’s Monticello, while the expansive grass hills were a nod to The Lawn at the University of Virginia. 

The original grounds covered 350 acres along the Virginia Beach waterfront, and included a 290-acre golf course with holes modeled after the historic Scottish golf courses of St. Andrews and North Berwick. The grounds were also used by guests hunting for native fowl, and after returning from the hunt, guests could have their game prepared by the on-site chef, who would cook the meal according to the guest’s specific tastes, then serve it up in front of a roaring fire in the Hunt Room. 

When it came to interior choices, the hotel was even more impressive. Every hotel room had its own private bathroom, a big deal at the time, and these bathrooms had their own impressive features. Bathtubs had an extra faucet handle that brought in water from the Atlantic Ocean for a saltwater bath, a spa practice that was popular with the upper class at the time, while the sinks had an ice water faucet that drew from a large wooden ice-filled tub located on the hotel roof, providing guests with chilled water even on the hottest days of summer (unfortunately, you’ll have to stick with plain old hot and cold taps nowadays). 

The hotel amenities were also extravagant; the indoor swimming pool was filled with filtered ocean water and outfitted with a diving board, and there were on-site offices for a variety of staff positions, including a doctor, photographer, radio broadcast center, and even a stockbroker, with a live ticker tape bringing updates straight from the New York Stock Exchange. Boutique stores allowed guests to shop without ever leaving the hotel, and a hair salon in the lower lobby was an added luxury. A private train depot, with a nonstop route from Chicago, among other central locations, allowed guests to travel directly to the hotel, while guests arriving by steamer ship or at other rail stations were met with a limousine from the hotel’s personal fleet, ensuring a luxury experience from departure to arrival. 

A historic photo of the Cavalier Beach Club in the 1920s

Image Courtesy of the Library of Virginia


Although the hotel was already considered one of the finest in the world, they topped the opulence off with the grand opening of the Cavalier Beach Club on Memorial Day weekend in 1929 (shortly before the infamous stock market crash). The lively club drew big performers like Frank Sinatra and Ella Fitzgerald, and between 1930 and 1950, the Cavalier would become the largest contractor of big bands in the world. The beach club was an icon of its time, and none that followed could ever take its place. 

Who’s Who: The Cavalier’s Numerous Celebrity Guests 

As one of the premiere luxury resorts on the East Coast, the Cavalier welcomed countless movie stars, business tycoons, and celebrities over the next few decades. American writer F. Scott Fitzgerald and wife Zelda often took extended vacations at the Cavalier, and Fitzgerald was even said to have been inspired to pen “The Great Gatsby” during one of his stays. Icons like Bob Hope, Elizabeth Taylor, Judy Garland, Muhammad Ali, Will Rogers, Jean Harlow, and Bette Davis came to stay at the Cavalier, as well as ten U.S. Presidents: Harry Truman, Jimmy Carter, Herbert Hoover, Gerald Ford, Calvin Coolidge, Franklin D. Roosevelt, Dwight D. Eisenhower, John F. Kennedy, Lyndon B. Johnson, and Richard Nixon. The exclusive hotel would remain synonymous with wealth and privilege until the early 1940s. 

Today, the newly-renovated Cavalier Hotel is back to drawing the biggest names from around the country. Although it has only been open since 2018, the hotel has already had stars such as Pharrell, Jimmy Buffett, Pusha T, Gwen Stefani, and Trey Songz come for an overnight stay. With celebrities returning to the historic luxury hotel, it’s safe to say that the upcoming era may be yet another opulent “Roaring Twenties” decade for the Cavalier Hotel.

The Golden Years - World War II

As the United States entered World War II at the end of 1941, the Cavalier Hotel was commandeered by the United States Navy, turning the exclusive resort into a radar training center. The pool was drained and used for conducting classes, and when the hotel ran out of room for soldiers, they used the on-site stables as extra accommodations. While the lodging may have been a bit cramped, the soldiers considered themselves some of the luckiest enlisted men in the American military; the hotel chef stayed on after the Navy moved in, and many of the soldiers would write home with tales of the exemplary meals served during their stay.

Post-War Problems & Intermittent Closures

The Cavalier was returned to its former owners in 1945, but the years of military occupation were not kind to the hotel, and much of the regular clientele did not return to the summer vacation destination after the war. It was converted into a private club for much of the 1950s and 1960s, then reopened to the public for a few years. In 1973, the Cavalier opened a sister hotel, the Cavalier Oceanfront, just across the street, and the original was renamed the Cavalier on the Hill. With brand new rooms outfitted with the latest in comfort and amenities in the Cavalier Oceanfront, the historic Cavalier Hotel was shuttered, but the modern luxury hotel could not replace the splendor of the original; it was once again reopened to guests in 1976. For the next 25 years, the two Cavalier Hotels would be mainstays for the Virginia Beach community and vacationing guests.

Luxury Reimagined: The Cavalier Reopens


In 2002, both the Cavalier on the Hill and the Cavalier Oceanfront underwent massive multi-million dollar renovations, but the upgrades were short-lived; in 2014, both hotels were closed, and the Cavalier Oceanfront and Beach Club were completely demolished. The Cavalier on the Hill was placed on the National Register of Historic Places during this time to protect the priceless property from a similar fate, and after an $85 million restoration, it was reopened in 2018 with the original name: The Cavalier Hotel. Due to the historic status, the renovations were painstaking and meticulous. Windows on the first floor were removed from their frames and repaired by hand. The decor was designed to reflect the Gilded era in which the resort was opened, with elegantly modern twists throughout. 

The hotel retains 21 of the original 350 acres, with the land surrounding the original structure used for an exclusive townhouse community. They are currently building a second hotel across Atlantic Avenue to replace the Cavalier Oceanfront, and are planning to eventually add a third hotel to the complex. 

Cavalier Beach Club

The Beach Club has also been rebuilt, with semi-private beach access, an infinity pool that looks out onto the Atlantic Ocean, and a poolside bar and grill, all only available to guests of the Cavalier Hotel or residents in their private community. The hotel’s indoor pool is another iconic feature that underwent renovations; it now features poolside service, private cabana rentals, and stylish lounge areas. 


Today, the Hunt Room retains its historic floor plan, and guests can enjoy a specially-curated menu paired with libations containing spirits distilled just steps away: Tarnished Truth Distilling Company is the first craft distillery to be located inside a hotel in the entire U.S. 


Becca, the Cavalier’s on-site fine dining option, is a nod to the Cavalier’s original signature restaurant, The Pocahontas, named for the famous Native American woman that resided near the Jamestown Colonial settlement and would later Anglicize her name to Rebecca. The restaurant’s menu features seasonal farm to fork dishes that reflect many Virginia products. 


More Notable Virginia Beach History

The Cavalier Hotel has an uncommonly distinct history, but it is far from the only historic site in Virginia Beach. As the landing site for the first colonial settlers arriving in Virginia, Virginia Beach is a trove of history. Visit First Landing State Park to walk where the original English settlers made landfall in 1607, and stop by the Cape Henry Lighthouse, which was the first federally funded public works project initiated by the United States Government under George Washington. 


Walk along the Boardwalk and stop at the Norwegian Lady Statue, a tribute to the 1891 shipwreck of the Norwegian ship Dictator along the coast of Virginia and the community members that worked tirelessly after the wreck to save many of the passengers. 

An identical sculpture stands Virginia Beach’s sister city of Moss, Norway.


Looking for even more Virginia Beach history? Experience it all at the local museums and historic sites, such as the Military Aviation Museum, the Adam Thoroughgood House, and the Virginia Beach Surf and Rescue Museum.

Virginia Beach Today


Image Courtesy of Virginia Beach

As a go-to vacation destination among the most famous artists, musicians, and other innovative thinkers in the 20th century, the Cavalier Hotel helped put Virginia Beach on the map as a mecca for creativity. That influence is evident today in the city’s impressive arts and music scene. The ViBe Creative District, just off the oceanfront strip, is a hub for both local and nationally renowned artists. Murals adorn the walls of over a dozen businesses in the area, adding colorful and artistic touches, and sculptures, creative crosswalk art, and special installations are constantly being added to the vibrant community. Another artistic center within the oceanfront destination is the Virginia Museum of Contemporary Art, known for their vast array of contemporary art from leading international, national, and regional artists. Each year, the museum hosts the Annual Boardwalk Art Show, which has been running since 1952.


When it  comes to music, Virginia Beach is a prime spot for live shows. The American Music Festival, one of the nation’s largest and longest-running waterfront music events, brings together an impressive lineup of musicians each year to perform right on the beach. Past performers include Sheryl Crow, Heart, The Beach Boys, Willie Nelson, Boyz II Men, and ZZ Top. While much newer, Something in the Water is another can’t-miss music festival for the Virginia Beach area. The brainchild of famous Virginia artist Pharrell, this music festival/cultural experience draws thousands of people to the shore to see some of the biggest names in rap, hip hop, rock, and more.   


If you need more inspiration for a Virginia Beach vacation that involves more than just surf and sand, use our three day vacation itinerary and dining guide to start planning an incredible coastal Virginia getaway.

Stay tuned for more But Did You Know… history articles to learn about some of Virginia’s most amazing untold stories!