America’s coolest cities – decade by decade

For all the majesty of its scenery – the Grand Canyon cutting a dash through the layered rock of the Colorado Plateau; the Great Lakes acting like inland oceans in their spray and surge – America has long been a country of the city.

From those first foundation stones of the colonial era – Charleston shimmering in the Carolina haze; Boston kicking tea chests into the brine – through New York, Chicago and the other fast-growing citadels of a freshly minted nation, and on to Los Angeles, San Francisco and and the other sunset splendours of the west coast, the USA has long thrummed to the busy thrill of urban life.

It has made stars of those cities as well. As the years rolled by, and the country spread, different places rose as the keepers of the American flame: bursting with ideas and inspiration in sustained bursts of energy and flair. You might describe this as “capturing the zeitgeist”, you might simply call it a case of “being cool” – but in a nation as big and diverse as the United States, there has always been a metropolis that outshines the others.

Of course, coolness can be a capricious mistress – arriving without any sign or warning, then disappearing just as quickly, off to a new address without a backwards glance. And as time has changed and tastes have morphed, so the mantle of America’s coolest city has shifted, flitting from east coast to west, and north to south, borne on a tide of art, music, architecture, literature, cinema, food, and cocktails (coolness always involves cocktails).

How to rebottle that lightning? This feature tracks the path of American coolness over the past 125 years, picking out the most exciting city in each of the last 13 decades – from the mists of the 1900s, all the way to the 2020s.

Where will it go next? Only 2030 will tell…

The 1900s: New Orleans

Sometimes, coolness only becomes clear after the event. Certainly, the (predominantly) black musicians plying their trade in the bars of Storyville – the then-red-light district of Louisiana’s biggest city – in the first decade of the new century would have been unlikely to see themselves as trendsetters.

America was not yet 50 years on from its abolition of slavery, the South was still segregated, and the melodies which unwound in those dingy venues did not reach the ears of the well-to-do. Nonetheless, jazz, in its modern form, was born in this febrile context, the likes of The Bolden Band, led by cornet maestro Charles “Buddy” Bolden, breaking the mould.

It would take another decade for the genre to reach the country beyond, another two before the “Jazz Age” kicked in, but the music that erupted in the Big Apple in the 1920s owed everything to the Big Easy of the 1900s.

Time capsule

Although much younger than it seems – it has only been a venue since the 1950s – Preservation Hall is the heartbeat of jazz in New Orleans.

Time travel

New Orleans features in the 10-day “Tastes and Sounds of the South” tour sold by Trafalgar (0800 533 5619). From £3,350 per person (flights extra).

The 1910s: Detroit

Often dismissed – not a little unfairly – as the rusted underside of the American Dream, Detroit suffered a torturous decline in the second half of the 20th century. Yet before it could fall from grace, it had to fly high: a Midwest Icarus whose rapid ascent reached its wax-melting zenith in the late 1920s, but commenced a decade earlier.

Before the Wall Street Crash of 1929, there was the rise of Ford and the advent of the Model T (launched in 1908, but manufactured in such numbers during the 1910s that, by 1918, it accounted for every second car on US roads).

With this came the first flurry of construction that would see the city’s skyline rival New York’s; the graceful Dime Building (now Chrysler House) in 1912, the Penobscot Building Annex a year later. But the greatest sign of the good times was Michigan Central, the cathedral-like station whose doors opened in 1914.

Time capsule

Said railway hub. The last train left in 1988, but the building re-emerged last year – restored to full glory after three decades of dereliction.

Time travel

Detroit bookends the 13-night “Pure Michigan” tour sold by America As You Like It (020 8742 8299). From £1,945 per person, with flights.

The 1920s: New York

Jazz may have been conceived in New Orleans, but it was New York which became the emblem of the “Jazz Age”. Nowhere roared more loudly during the Roaring Twenties than the Big Apple, whose streets hummed with music and creativity. F. Scott Fitzgerald set the tone of the era with his 1922 collection Tales of the Jazz Age, then captured its decadence in The Beautiful and Damned (also 1922) and 1925’s The Great Gatsby – both novels set in and around the city.

Meanwhile, New Yorkers partied, the exuberance soundtracked by Louis Armstrong and Duke Ellington at the Cotton Club in Harlem, and by big-band sounds, guided by the charismatic Guy Lombardo, in the ballroom of the Roosevelt Hotel. Architecture was also upwardly mobile, the boom times encapsulated by the Art Deco magnificence of the Chrysler Building, which began its ascent in 1929.

Time capsule

The Cotton Club fell victim to changing times and soaring rents in 1940; the Roosevelt was killed off by the Covid pandemic in 2020. But other icons of the era remain – including The Lexington, a Midtown jewel that opened in 1929.

Time travel

A seven-night stay at the Lexington, flying in from Manchester on May 24, starts at £1,937 per person via Virgin Atlantic Holidays (0344 472 9646).

The 1930s: Chicago

One of the ironies of the Roaring Twenties is that its anything-goes ethos was teetotal. Officially, anyway – Prohibition strode onto the American statute books in 1919, and squatted there until 1933. The inevitable result was the rampant bootlegging ultimately exposed in The Great Gatsby – and a raft of speakeasies, which popped up all over New York and Chicago.

The latter adopted the concept of the unmarked building and the clandestine cocktail with particular aplomb – a green door becoming the tacit symbol for a hidden establishment where liquor was available. It still is, in the case of The Green Door Tavern – which, dating to 1921, nudge-nudged and wink-winked its way through the sober years, and still sells itself as Chicago’s oldest bar.

Time capsule

The Gatsby does a modern take on the speakeasy in Lincoln Park, close to the former Biograph Theater – where John Dillinger, one of the most notorious gangsters of a lawless period, was shot dead in 1934.

Time travel

The Blackstone also witnessed the shadows of the era – Al Capone frequented its barbershop. A five-night stay, flying in from Heathrow on May 21, costs from £1,197 per person, through Expedia (020 3024 8211).

The 1940s: Washington DC

The US capital can be tricky to position as a cool cat. Too swampy in its origins, too humid in summer, too obsessed with government business to be truly sexy, it is usually portrayed as functional rather than fabulous. But if it had a decade in the sun, it was the 1940s, when the world was consumed by conflict, and it became the heartbeat of the American war effort.

As Europe burned and Japan was bombed, DC grew in size and stature. Its expansion was visible in the swelling of its population; its head-count of 487,000 in the census of 1930 becoming 663,000 in 1940, and 802,000 by 1950 – the latter a record figure that has never been eclipsed.

It was apparent in new infrastructure too – Washington National Airport (since renamed in honour of Ronald Reagan) opened in 1941, a crucial conduit for all those new employees heading to their federal desk jobs.

Time capsule

Part of the 16th Street Historic District dates to the decade, including The General Scott apartments, crafted by architect Robert Scholz.

Time travel

Washington DC is a key element of the 14-night “Capital Region Cruiser” tour sold by The American Road Trip Company (01244 342 099). From £1,899 per person, including car and flights.

The 1950s: Memphis

You could never say that The Blues, that endlessly rhythmic, melancholy form of music, was exclusively a Memphis phenomenon. It took form in the (very) Deep South in the 1860s, and Chicago can claim it as its own just as much as Tennessee’s most intriguing city.

But Memphis packaged it with such aplomb in the 1950s that, soon, the whole world was in on the sound. By the start of the decade, the genre’s finest protagonist, BB King, was a key performer in the clubs on Beale Street. By 1954, Elvis Presley had stirred youthful insouciance into the pot with his cover of 1946 blues number That’s All Right – and rock ’n’ roll was sliding into view.

Both men are gone, but their stories linger – at the Graceland mansion where Presley’s stardom ultimately curdled, and on Beale Street, where BB King’s Blues Club keeps the tunes alive.

Time capsule

Sun Studio, the sacred space where Presley cut that debut single, and numerous other giants – King, Howlin’ Wolf, Little Milton – recorded tracks.

Time travel

Memphis is a core part of the 14-day “Classic Deep South USA” tour sold by Journeyscape (020 3813 7147). From £3,570 per person, flights extra.

The 1960s: San Francisco

Within a decade, that new rock music had passed through a psychedelic kaleidoscope, and was taking on fresh and strange intonations in Liverpool, London and New York. But the countercultural movement of the 1960s – a giddy blur of art, attitude, drugs, literature, anti-consumerist sentiment and anti-war rhetoric, which went far beyond music – found its brightest expression in the sloping streets of San Francisco. Not least in the Haight-Ashbury district.

The neighbourhood became the mecca of the hippy lifestyle; a swirl of “people in motion… a whole new generation”, to quote the 1967 Scott McKenzie hit San Francisco (Be Sure To Wear Flowers In Your Hair). The free-love fantasy reached its apex that same year in the “Summer of Love”, when thousands of dreamers swelled the area, and the music of local bands – Jefferson Airplane, the Grateful Dead – filled the air.

Time capsule

Golden Gate Park, which spreads out directly west of Haight-Ashbury – and Hippie Hill, the rise within it which witnessed so much of that summer’s merriment.

Time travel

The city starts and ends the 10-day “Gems of Northern California” tour sold by American Sky (01342 395 519). From £1,699 a head, with flights.

The 1970s: Las Vegas

Anyone who has spent time in Sin City might suggest that it could find its slot in many of the decades listed here – with the exception, maybe, of the present one, where Las Vegas has gained a family-friendly sheen, but lost some of the edge that made it so exotic.

For the glory days, you may need to retreat half-a-century, to a place that was harder and sleazier; a city that has been particularly visible on the cinema screen (notably in Martin Scorsese’s blockbuster Casino; released in 1995, but set in the 1970s and 1980s), cigarette smoke billowing above poker tables.

There was star quality too. Frank Sinatra was still crooning, at Caesars Palace and the Sahara; Presley was reeling off the hits at the International Hotel. Many of the landmark properties of that era – the Sands, the Dunes, the Desert Inn – have long since vanished. Some would say that much of the Vegas vibe went with them.

Time capsule

Circus Circus – a hotel so tied to 1970s Las Vegas that it appears in the 1971 James Bond classic Diamonds Are Forever – is still alive and well.

Time travel

A lower-cost option amid more modern palaces, the Sahara is also still going. A seven-night getaway, flying in from Gatwick on April 5, starts at £1,344 a head, with British Airways Holidays (0344 493 0787).

The 1980s: Los Angeles

The city which underpins the Hollywood machine is never really out of fashion, but Los Angeles was the cinematic flavour du jour of the 1980s, providing a backdrop to the likes of Beverly Hills Cop (1984), The Terminator (1984), Lethal Weapon (1987) and Tequila Sunrise (1988). In the meantime, its “glam-metal” bands had taken over Sunset Strip and the charts – the likes of Mötley Crüe, Ratt and (later) Guns N’ Roses knocking out music variable in quality but consistent in volume, sales figures and hugeness of hair.

LA hosted this party in what seemed to be a permanent sunshine, looking toned when it staged the Olympics in 1984, then outstripping Chicago’s population to become the US’s second largest city in the same year. The jury remains out on whether TV hit Baywatch, which cast a lascivious eye at its beachfront from 1989 onwards, was bad-taste fun – or just bad.

Time capsule

Try the Rainbow Bar & Grill and the Whisky A Go Go, the Sunset Strip scenes of many late-night hair-metal parties.

Time travel

LA is the highlight of the “10 Days in Southern California” holiday sold by Original Travel (020 3958 6120). From £2,665 a head – with flights.

The 1990s: Seattle

When the hair-metal train derailed in 1991, it did so partly because of a shift in musical tastes orchestrated by an underdog in the Pacific Northwest. Economically depressed in the 1960s and 1970s, Seattle was an unlikely candidate for newfound cool, clinging to the coast of Washington state in a haze of forest and rainfall.

But this outsider status distilled itself into grunge – the distorted take on hard rock which made stars of local bands Pearl Jam, Soundgarden and Alice In Chains, and catapulted Kurt Cobain, enigmatic frontman of scene-leaders Nirvana, onto a million magazine covers.

In truth, the moment did not survive the latter’s suicide in 1994, but by that point, the city was spotlit, part-framing Tom Hanks’s 1993 mid-life romcom Sleepless In Seattle, and providing the backdrop to the arty sitcom quips of Frasier. Its coffee culture also proved exportable. In 1989, Seattle brand Starbucks had 55 outlets – largely in the Northwest. By 2000, it had 3,501.

Time capsule

Although no longer at its original address, The Crocodile is a Seattle institution; a gig venue which hosted most of grunge’s key luminaries.

Time travel

Seattle features in the 13-day “Great Pacific Northwest” road-trip offered by Bon Voyage (0800 980 7093), from £3,095 per person, with flights.

The 2000s: Atlanta

Several cities could have laid claim to being the epicentre of American cool in the first decade of the new millennium. Over in Oregon, Portland’s metamorphosis into an oasis of craft-brewed hipsterism was so right-on that, by 2011, it was being lampooned in a self-deprecating sitcom (Portlandia). Nashville might have seized the crown via the rapidly broadening appeal of its country music scene, from which Taylor Swift emerged. But the musical baton passed most persuasively to the Georgia capital, Atlanta.

An upward surge kick-started by the Summer Olympics of 1996, and the urban regeneration it brought, flowered in wild blooms of invention – not least a raft of rap acts so exciting that, by 2009, The New York Times was calling Atlanta “hip-hop’s center of gravity”. Outkast and Ludacris may have had international hits in the 2000s, but their success was distilled in the Peach State.

Time capsule

The appropriately named Hip Hop Tours Of Atlanta serve up guided jaunts around the city’s rap-relevant districts.

Time travel

Atlanta kicks off the 13-day “Luxury Georgia and the Carolinas” tour sold by Audley Travel (01993 460 707). From £7,200 per person with flights).

The 2010s: Austin

The cultural fertility of Texas’s capital has long passed the point of being a curiosity, and is now a phenomenon. Austin has been an outlier for some time – an island of blue liberalism in a red conservative state (former Texas governor Rick Perry once called it “a blueberry in the tomato soup”).

You could make a case for its having been the coolest US city in any of the past 40 years; and certainly since 1987, when the birth of the South by Southwest festival cemented its place as a hotbed of live music (an image that was burnished in 2002 with the arrival of the Austin City Limits extravaganza).

Alive with art, melody and nightlife (it is impossible to have a quiet evening on Sixth or Rainey Streets, or in the bars of East Austin), the city is defiant in its otherness. First used in 2000, the slogan “Keep Austin Weird” is as relevant now as then.

Time capsule

Located west of Downtown in Clarksville, Bar Peached was named “Best Patio Bar” by Austin Monthly Magazine in 2019.

Time travel

Austin, San Antonio and Houston feature in the 15-day “Texan Trails” tour sold by Trailfinders (020 7084 6500; trailfinders.com). From £2,099 per person, flights extra.

The 2020s: Miami

Set strikingly at the lower tip of the Florida peninsula, Miami has always had a fair element of pizzazz, without ever, perhaps, being America’s king of cool. However, the city is making the most of the 2020s. Its Ultra Music Festival of EDM (electronic dance music) has been a spring party-starter since 1999 (March 28-30 in 2025).

But a slew of chic hotel openings – the Moxy last November; the Andaz this March; a Bulgari property that will arrive in 2027 – are adding a fresh gleam to a waterfront that was always stylish in the Art Deco boltholes on Ocean Drive.

And there is glamour away from the sea. If David Beckham’s role in the founding of Inter Miami in 2018 was not enough to seize the cool-crown, the football club’s signing of Argentine superstar Lionel Messi in 2023 surely sealed the deal.

Time capsule

Cafe La Trova, the cocktail joint with a Cuban accent which polled at no.24 in the 2023 list of the World’s 50 Best Bars.

Time travel

Seven nights at another Miami five-star, The Setai, starts at £3,484 per person (flights extra), with Elegant Resorts (01244 292 429).