From the Chicago kitchen that gave birth to the brownie to a Washington landmark that once helped connect a growing nation through the U.S. mail, these iconic properties reveal how hospitality has intersected with innovation, culture and defining moments in American life.
In this second installment of our America250 series, we spotlight more hotels where the stories extend far beyond the guestrooms.
Ready to continue the journey? Explore Part I of our series here.
Palmer House, A Hilton Hotel
Opened: 1871 in Chicago
History Made Here: America’s longest continuously operating hotel—and the birthplace of the brownie.
Few hotels can claim to have shaped American history quite like the Palmer House. Originally opened in 1871, just 13 days before the Great Chicago Fire, the hotel was destroyed in the blaze and rebuilt by entrepreneur Potter Palmer.
Over the decades, the Palmer House helped usher in the modern age of hospitality, becoming the first hotel to incorporate innovations such as the light bulb, the telephone and the vertical steam lift, better known today as the elevator.
By the turn of the century, it had evolved into Chicago’s social epicenter, welcoming everyone from U.S. Presidents and literary icons Charles Dickens and Oscar Wilde to entertainment legends including Frank Sinatra, Judy Garland, Ella Fitzgerald and Louis Armstrong.
Its most enduring contribution to American culture, however, may be culinary. In 1893, Bertha Palmer commissioned the hotel’s pastry chef, Joseph Sehl, to create a portable dessert for ladies attending the World’s Columbian Exposition. The result was the now-famous Palmer House brownie—a rich, fudge-like confection topped with walnut and apricot glaze that many credit as America’s original brownie.
For more information, visit palmerhousehiltonhotel.com.
Pier Sixty-Six
Opened: 1965 in Fort Lauderdale
History Made Here: A Space Age icon reborn for a new generation.
Few properties capture the exuberance of mid-century America quite like Pier Sixty-Six. When the resort opened in 1965, its futuristic Googie architecture and revolving Pier Top lounge embodied the optimism of the Jet Age, when Americans embraced innovation, mobility and a newfound appetite for leisure travel.
Its story, however, began even earlier. The site originated in 1957 as a Phillips Petroleum fuel dock and service station serving South Florida’s growing boating community. Named for the company’s iconic Phillips 66 brand, the property expanded to include a 100-berth marina and motel before evolving into one of Fort Lauderdale’s most recognizable resorts.
At the center of it all was the Pier Top lounge. Perched high above the Intracoastal Waterway, the revolving venue became Fort Lauderdale’s place to see and be seen throughout the 1960s and ’70s. With panoramic views of the Atlantic Ocean and passing yachts below, it drew celebrities, local tastemakers and notable figures of the era, including Frank Sinatra and Walter Cronkite.
Following a $1 billion restoration and reopening in 2025, Pier Sixty-Six once again anchors Fort Lauderdale’s waterfront. The transformation preserved the property’s distinctive architectural identity while reimagining its most iconic spaces for a new generation of travelers.
For more information, visit piersixtysix.com.
The Drake Oak Brook
Opened: 1961 in Illinois
History Made Here: A suburban hideaway favored by entertainers, politicians and sports legends.
Just outside Chicago, The Drake Oak Brook served as a discreet retreat for some of the 20th century’s most recognizable names, including Frank Sinatra, Robert Kennedy, Arnold Palmer and Jack Nicklaus.
Built in 1961 as a suburban counterpart to Chicago’s iconic Drake Hotel on Michigan Avenue, the property brought big-city sophistication to Oak Brook and helped shape DuPage County’s hospitality landscape.
Under the stewardship of legendary catering manager Gino DiRenzo, who spent nearly five decades at the hotel from 1962 to 2009, it became a sought-after setting for celebrations, social gatherings and visits from an impressive roster of luminaries, including Rock Hudson and Prince Charles.
Following the collapse of a Ponzi scheme tied to the property’s ownership, the hotel closed its doors. In 2013, Elmhurst natives Jim and Tely Nagle purchased the dormant landmark. They embarked on a painstaking, hands-on restoration that honored its historic character while returning it to its former grandeur.
The hotel reopened in 2015 under new management with 87 refreshed guestrooms. A subsequent transformation into a refurbished Marriott Autograph Collection property with 153 guestrooms.
In honor of America’s 250th anniversary, the property plans to debut its Liberty at the Drake celebration, along with a Liberty Escape Package featuring patriotic cocktails, an American artisan snack board, dinner in the Colonial Room and tickets to the hotel’s signature Afternoon Tea.
For more information, visit thedrakeoakbrookhotel.com.
Waldorf Astoria Washington DC
Opened: 1899 as the Old Post Office; reimagined as a Waldorf Astoria in 2022
History Made Here: A Beaux-Arts landmark at the crossroads of American history.
Occupying the landmark Old Post Office Building on Pennsylvania Avenue, Waldorf Astoria Washington DC offers guests the rare opportunity to sleep inside one of the nation’s most recognizable civic treasures.
Completed in 1899, the Romanesque Revival masterpiece served as headquarters for the U.S. Post Office Department and Washington’s main post office, playing a vital role in an era when the mail system connected a rapidly expanding nation. Positioned between the White House and the U.S. Capitol, the building has stood witness to more than a century of presidential inaugurations, national celebrations and defining moments in American history.
Guests can take Afternoon Tea beneath Peacock Alley’s dramatic nine-story atrium before ascending the historic Clock Tower for panoramic views of the White House, the National Mall and the U.S. Capitol.
The building’s former life remains visible throughout the hotel. What is now the 10,000-square-foot luxury spa and fitness center once served as the bustling ground-floor mailroom, where original curved ceilings still hint at the days when mail carts arrived directly from nearby train tracks. Meanwhile, the hotel’s 4,000-square-foot Presidential Suite occupies what was once the grand office of the Postmaster General.
For more information, visit hilton.com.
