Despite the breathtaking scenery of landmarks like the Grand Canyon and the Great Lakes in the United States, the country has always been characterized by its vibrant cities. From the colonial beginnings of cities like Charleston and Boston, through the growth of metropolises like New York, Chicago, Los Angeles, and San Francisco, urban life has been a cornerstone of American culture. These cities have not only thrived but have also become symbols of American identity, brimming with creativity and energy that captures the spirit of the nation.
Over the years, different cities have emerged as trendsetters, embodying the essence of coolness and innovation at various points in history. From the east coast to the west, from the north to the south, the title of America’s coolest city has shifted with changing times, influenced by art, music, architecture, literature, cinema, and yes, cocktails. This feature traces the evolution of American coolness over the past 125 years, highlighting the most exciting city of each decade from the 1900s to the 2020s.
As the journey through American coolness unfolds, from the birth of modern jazz in New Orleans in the 1900s to the rise of Detroit in the 1910s as a symbol of industrial progress, it becomes evident that the concept of coolness is ever-changing and unpredictable. Each city that has held the mantle of coolness has left a unique imprint on the cultural landscape, shaping the narrative of American identity.
Join us on this time-traveling adventure through the coolest cities of the past, and stay tuned to see where the next decade will lead us. Only time will reveal the next chapter in the ever-evolving saga of American coolness.
In Detroit, prior to the Wall Street Crash of 1929, witnessed the rise of Ford and the introduction of the Model T. Launched in 1908, the Model T was produced in such large numbers during the 1910s that by 1918, every second car on US roads was a Model T. This era saw the beginning of a construction boom that would transform the city’s skyline, rivaling that of New York. Iconic buildings like the Dime Building (now Chrysler House) in 1912 and the Penobscot Building Annex in 1913 showcased the city’s prosperity. However, the ultimate symbol of this prosperity was the grand Michigan Central station, which opened its doors in 1914.
Time stood still at the railway hub as the last train departed in 1988, but the building was recently restored to its former glory after three decades of neglect. Visitors can now experience a journey back in time through the city’s history. Detroit serves as both the beginning and end of the “Pure Michigan” tour offered by America As You Like It, starting at £1,945 per person, including flights.
Moving to the 1920s in New York, the city became the epitome of the “Jazz Age.” F. Scott Fitzgerald captured the essence of the era in his novels, such as “The Beautiful and Damned” and “The Great Gatsby,” set against the backdrop of the bustling metropolis. Jazz music filled the streets, with iconic venues like the Cotton Club in Harlem hosting legendary performers like Louis Armstrong and Duke Ellington. The city’s skyline also reflected the boom times with architectural marvels like the Chrysler Building, a symbol of Art Deco opulence.
While some landmarks of the era, like the Cotton Club, have faded away with time, others, like The Lexington hotel, continue to stand as a reminder of the glamorous 1920s. Travelers can immerse themselves in this era with a stay at The Lexington, starting at £1,937 per person, flying in from Manchester via Virgin Atlantic Holidays.
The 1930s in Chicago saw the city flourishing as a hub for speakeasy bars during the Prohibition era. The clandestine cocktail culture thrived in the city, with establishments like The Green Door Tavern, known for its hidden location and illicit libations. Today, The Gatsby in Lincoln Park offers a modern twist on the speakeasy experience, paying homage to the city’s colorful past.
For a glimpse into Chicago’s history of the 1930s, visitors can stay at The Blackstone hotel, where notorious figures like Al Capone once roamed. A five-night stay, flying in from Heathrow, is available starting at £1,197 per person through Expedia.
Moving to the 1940s, Washington DC played a crucial role in the United States’ wartime efforts. The city was a bustling center of political activity and decision-making during this tumult
Positioning Washington, DC as a fashionable and sexy city can be challenging due to its swampy origins, humid summers, and focus on government affairs rather than allure. However, if there was a time when the capital city shone brightly, it was in the 1940s during the height of World War II. As Europe and Japan faced destruction, Washington, DC grew in size and significance, with its population rising from 487,000 in 1930 to 802,000 in 1950. This growth was accompanied by new infrastructure developments such as the opening of Washington National Airport in 1941. The city became the hub of the American war effort, symbolizing resilience and determination during a tumultuous era.
In a different musical realm, Memphis emerged as a prominent figure in the 1950s music scene, particularly in the realm of blues and rock ‘n’ roll. Musicians like BB King and Elvis Presley propelled the city into the global spotlight, with iconic venues like Beale Street keeping their legacies alive. Today, Memphis retains its musical heritage, welcoming visitors to explore its rich history and vibrant culture.
Moving into the 1960s, San Francisco became a beacon of countercultural movements, embracing art, drugs, literature, and anti-war sentiments in the Haight-Ashbury district. The city embodied the hippie lifestyle, attracting a wave of free-spirited individuals seeking a new way of life. Bands like Jefferson Airplane and the Grateful Dead provided the soundtrack to this era of love and rebellion, culminating in the legendary “Summer of Love” in 1967.
These cities, each with its own unique charm and history, offer a glimpse into the cultural evolution of America through the decades, inviting travelers to immerse themselves in their stories and legacies.
Golden Gate Park, located directly west of Haight-Ashbury, is home to Hippie Hill, where much of the summer’s festivities took place.
Traveling back in time, the city of San Francisco serves as both the beginning and end point of the 10-day “Gems of Northern California” tour offered by American Sky (01342 395 519), starting at £1,699 per person including flights.
In the 1970s, Las Vegas was a place of allure and excitement, as depicted in the James Bond film ‘Diamonds Are Forever’ set at Circus Circus hotel. Although the city has evolved into a more family-friendly destination, the nostalgia for its past glory days remains.
For a trip down memory lane to the vibrant 1980s, Los Angeles emerges as the cinematic darling, hosting iconic films and music scenes. The city’s cultural zenith is captured in the fast-paced era of glam metal bands and Hollywood blockbusters.
Seattle took the spotlight in the 1990s with the rise of grunge music, a genre that revolutionized the music industry and propelled local bands to international fame. Despite its humble beginnings, Seattle became a beacon for alternative music and culture during this transformative decade.
Nirvana’s frontman graced a million magazine covers, leading the grunge music movement from Seattle, known as the birthplace of bands like Pearl Jam. Despite the tragic loss of Nirvana’s lead singer in 1994, Seattle continued to shine in the spotlight, featured in films like “Sleepless In Seattle” and the sitcom “Frasier.” The city’s coffee culture also thrived, with Starbucks expanding from 55 to 3,501 outlets by 2000.
The Crocodile, a legendary gig venue, remains a Seattle institution where many grunge icons performed. Travelers can explore Seattle’s music scene on a “Great Pacific Northwest” road trip offered by Bon Voyage.
In the 2000s, Atlanta emerged as a hip-hop hub, solidifying its cool status with artists like Outkast and Ludacris. Tourists can discover Atlanta’s rap culture through Hip Hop Tours and luxury tours offered by travel agencies.
Austin became a cultural phenomenon in the 2010s, known for its live music scene and vibrant nightlife. The city’s slogan, “Keep Austin Weird,” reflects its unique character. Travelers can experience Austin’s charm at spots like Bar Peached or through Texan Trails tours.
Miami, located at the tip of Florida, exudes glamour and excitement. The city has always been known for its vibrant atmosphere, making it a perfect destination for the 2020s.
Possibly the epitome of coolness in America, Miami is truly embracing the spirit of the 2020s. The city’s Ultra Music Festival of EDM (electronic dance music) has been kick-starting spring celebrations since 1999, with the next event scheduled for March 28-30 in 2025. Among Miami’s luxurious offerings is the renowned five-star hotel, The Setai, providing a quintessential Ocean Drive experience. The hotel scene in Miami is bustling with the recent openings of trendy establishments like the Moxy last November, the Andaz this March, and the upcoming Bulgari property set to debut in 2027. These new additions are infusing a fresh vibrancy into Miami’s waterfront, known for its timeless style embodied by the Art Deco hideaways along Ocean Drive. Beyond the coastal allure, Miami exudes glamour in various forms. Noteworthy is David Beckham’s involvement in the creation of Inter Miami in 2018, which was further solidified by the football club’s acquisition of Argentine superstar Lionel Messi in 2023. A notable spot to capture the essence of Miami’s contemporary scene is Cafe La Trova, a cocktail bar with a Cuban flair that ranked 24th in the 2023 list of the World’s 50 Best Bars. For a luxurious retreat, consider a seven-night stay at another esteemed Miami five-star accommodation, The Setai, starting at £3,484 per person (flights not included) through Elegant Resorts (01244 292 429). Immerse yourself in award-winning British journalism and explore a world of content with a complimentary one-month subscription to The Telegraph, granting you unlimited access to the acclaimed website, exclusive app features, money-saving deals, and more.
