In 1927, a hotel opened on a hill overlooking the Atlantic Ocean and immediately became the place where presidents, celebrities, and East Coast society came to be seen. F. Scott Fitzgerald partied there. Seven U.S. presidents stayed there. Big bands played on the roof while bootleg whiskey moved through tunnels underneath. That building is still standing today at 42nd Street and Atlantic Avenue in Virginia Beach, and most locals have no idea how wild its story actually is.
The Cavalier Hotel Virginia Beach history stretches nearly 100 years, and it touches everything from Prohibition-era crime to Hollywood glamour to a near-wrecking-ball moment that almost erased the whole thing.
How the Cavalier Came to Be
The Cavalier opened on April 4, 1927, built by a group of local businessmen who wanted to attract wealthy Northern tourists to the Virginia Beach oceanfront. The construction cost $2 million at the time, which is roughly $35 million in today's dollars. The building sits on a six-acre hilltop site, which was a deliberate choice — the elevated position made it visible from miles away and gave guests a panoramic view of the ocean.
The hotel had 195 rooms, formal dining rooms, a ballroom, and a private beach club connected by a dedicated shuttle. From the moment it opened, it operated as a destination resort, not just a place to sleep. And it worked. Within a few years, it had become one of the most fashionable addresses on the entire East Coast.
The timing was notable. The Cavalier opened right in the middle of Prohibition. That did not slow down the cocktail culture inside the hotel at all. Tunnels reportedly ran beneath the property, used to move alcohol discreetly when federal agents came around. Whether you call it resourceful or lawless depends on your perspective, but it became part of the hotel's mythology.
The Golden Era: Presidents, Big Bands, and F. Scott Fitzgerald
Between the late 1920s and World War II, the Cavalier hosted a roster of guests that reads like a pop culture history book. Presidents Coolidge, Hoover, Eisenhower, Nixon, Reagan, Harrison, and Ford all stayed there. Judy Garland performed in the ballroom. Cab Calloway played on the rooftop. F. Scott Fitzgerald, who was already deep into his most famous work during this period, was a known presence at the hotel.
During World War II, the U.S. Navy took over the building entirely and used it to train radar operators. The hotel closed to the public for the duration of the war. When civilian guests returned in 1945, the Cavalier never quite recaptured the pre-war magic at the same scale, but it remained a beloved landmark through the 1950s and 1960s.
In 1973, a new oceanfront tower was built adjacent to the original hilltop building. Most of the hotel's operations shifted to the new structure, and the original Cavalier on the Hill sat mostly empty for decades. It deteriorated badly. At several points, demolition looked like the most likely outcome.
The $85 Million Restoration
In 2012, the Cavalier was purchased by a group of investors who committed to restoring the original hilltop building rather than tearing it down. The project took years and cost approximately $85 million. The restoration was completed and the hotel reopened in 2018, bringing back much of the original architectural detail while adding modern amenities.
The on-site distillery produces Tarnished Truth whiskey, which is a direct nod to the hotel's Prohibition-era bootlegging reputation. The fine dining restaurant, Becca, takes its name from the Cavalier's original signature restaurant, The Pocahontas, named for the historical figure who later took the Anglicized name Rebecca. The menu features Virginia products and seasonal dishes.
Today the Cavalier on the Hill operates as a boutique hotel and is listed on the National Register of Historic Places. The adjacent oceanfront tower continues to operate separately.
Why This History Still Matters
The Cavalier Hotel Virginia Beach history matters because it is a story about what kind of place Virginia Beach actually is. This city did not become a resort destination by accident. People made deliberate investments and decisions over nearly a century to build something worth coming back to.
When you drive past that red-brick building on the hill, you are looking at a structure that survived Prohibition, a World War, decades of neglect, and a serious demolition threat. It is still there. That says something about the people who live here and the community that decided it was worth saving.
If you want to go deeper on local history, Virginia Beach has several strong options including the Military Aviation Museum, the Adam Thoroughgood House, and the Virginia Beach Surf and Rescue Museum.
For more on what makes Hampton Roads worth calling home, browse the Legacy Home Search blog.
Frequently Asked Questions
When did the Cavalier Hotel Virginia Beach originally open?
The Cavalier Hotel opened on April 4, 1927. It was built by a group of local businessmen for approximately $2 million and was designed to attract wealthy resort travelers to the Virginia Beach oceanfront.
What famous guests stayed at the Cavalier Hotel?
Seven U.S. presidents stayed at the Cavalier, including Eisenhower, Nixon, and Reagan. Entertainers including Judy Garland and Cab Calloway performed there, and F. Scott Fitzgerald was among the notable guests during the hotel's golden era in the late 1920s and 1930s.
How much did the Cavalier Hotel restoration cost and when did it reopen?
The restoration of the original Cavalier on the Hill cost approximately $85 million. The project began after a 2012 purchase by a group of investors and the restored hotel reopened in 2018. It is now listed on the National Register of Historic Places.
Related reading
• Bayport Credit Union Financial Tips Every Hampton Roads Homeowner Should Know
• Famous Athletes and Icons From Hampton Roads You Should Know About