Does the world’s most famous route still capture the romance of the open road?

'There are 191 turns in eight miles,’ says the woman, who smiles as she warns of the Oatman Highway just up the road. She is a clerk in Cool Springs Station, the last roadside stop before this treacherous part of Route 66 in north-west Arizona. ‘Just stick to the speed limit and there’s nothing to worry about.’ She knows the face of a concerned traveller when she sees one.

I’m right to be worried. Dangerous Roads, a website dedicated to highlighting the world’s most difficult routes, describes it as having ‘very few guardrails giving you no leeway for error’. It is, indeed, technical, with steep drops that will put the fear in your passenger if they peer out of the window.

And it’s high — the summit of Sitgreaves Pass topping out at 3,595 feet above sea level. Those brave enough to drive it will be rewarded with a visit to the Gold Rush town of Oatman itself located after the summit. They can also brag that they’ve driven one of the oldest stretches of Route 66.

The Oatman Highway is very different from much of Route 66, which once followed a broadly diagonal line of tarmac from Chicago all the way to Los Angeles, California. It was intended to make cross-country travel easier, as well as boosting the income of the small towns it severed. The route was decommissioned nearly 40 years ago in 1985 and celebrates its centenary in November 11, 2026, so what does ‘the Main Street of America’ look like today?

Cyrus Stevens Avery (1871–1963) is widely considered the ‘Father of Route 66’. Settling in Tulsa, Oklahoma, he was an early advocate of the highway and lobbied to bring well-maintained roads to his home state. Following the First World War, the USA quickly modernised and the idea of a national highway system first percolated in the 1920s.

Avery, who was behind the movement, was particularly passionate about a transcontinental route from Chicago to the Pacific Coast. He even coined the catchy ‘66’ moniker and it stuck, despite Highway official’s attempts to push ‘60’ or ‘62’. On November 11, 1926, Route 66 was officially commissioned.

America has of course changed drastically since. Many of the small towns along the route have flourished, others have suffered ever since the Route’s decommissioning in the 1980s.

I joined the road in Flagstaff, Arizona, first flying into Phoenix and then staying at The Fairmont Scottsdale — a 2½ hour drive south of Flagstaff. It’s necessary to stop before you’ve even started — to adjust to both the new time zone and to the intense, dry heat.

It’s impossible to drive north and meet Route 66 without a stop in Sedona. The city is home to two state parks and surrounded by Mars-like red rock formations and vibrant green foliage. If you want to stop (again), try Enchantment Resort, in the heart of Boynton Canyon. The ideal base for exploring what are some of the America's most beautiful landscapes.

After all this overwhelming beauty, you might feel somewhat underwhelmed by Flagstaff itself, but there is plenty to see from the Romanesque Revival architecture in its historic downtown district to the many weathered motel signs that hint at the town’s past. One of the best is the Western Hills Motel sign from 1950, which still lights up defiantly at night.

In 1938, on the eve of the Second World War, Route 66 was described as ‘continuously paved’. It was good timing not only for the war effort, but for the thousands who were forced to flee west from the severe dust storms and periods of drought that became known as the Dust Bowl (1934–40) — one of the worst human-made ecological disasters in history.

The motor hotels, or motels, built along the road’s edge before the war were joined by hundreds of new ones in the late 1940s and 1950s, owners keen to draw in motorists with increasingly elaborate designs and bigger and brighter neon signs.

Streamline Moderne architecture was a popular choice and saw motels and cafés built to look like boats, cars — and even toasters. Mexican restaurants marketed themselves with giant sombrero hats, leaving little doubt of the cuisine served inside, and Native American-appropriated wigwams popped up outside convenience stores and diners. Fiberglass ‘muffler men’ loomed 25-foot-tall, advertising garages.

In 1950, more than 6,500,000 new cars were sold in the USA. Five years later, the number rose to 8,000,000. This boom, together with the excessive wartime use, signalled the end of Route 66. Much of the tarmac laid 20 or so years before was cracked and now undrivable and the road’s narrow widths weren’t designed for modern, larger cars.

It was the introduction of modern, multi-lane highways that put the final nail in the coffin. After returning from Germany, President Eisenhower, impressed by Adolf Hitler’s autobahn, quickly devised a complete overhaul of the country’s highway system and, over the next two decades, the majority of 66 was paved over or completely bypassed.

This makes driving the Route today challenging. It’s not until you get to Seligman — a small town that has one of the best collections of original 66 architecture, dating from the early 1900s — that the clocks feel as if they’ve truly turned back. Seligman is also the place that, in 1987, convinced the state of Arizona to designate the stretch from Seligman to Kingman ‘Historic Route 66’. This inspired the seven other states along the Route to do the same and, seven years later, the National Historic Route 66 Federation was founded — a group that’s busy preserving and restoring what is left.

The 100, unbroken miles Kingman takes in the run-down Historic Trading Post of Peach Springs, Hackberry General Store, the eccentric Antares Point Visitor Centre and Mike’s Outpost Saloon — all the while traversing dusty desert vistas often devoid of all other traffic. In Kingman, enjoy a home-cooked meal of pork chops ‘Florentine’ in a roadside diner before going one of two ways: California or, via Oatman and its tricky roads, Las Vegas.

Sin City was never on Route 66, but those travelling west today rarely miss it. The city is an acquired taste, but its bright lights and kitsch needs to be experienced at least once. It’s all laid out in front of me from the comfort of my air-conditioned room on the 36th floor of Fontainebleau, the Strip’s newest hotel. Better still is the hotel’s spa — every driver needs a massage to relax the shoulders — and its restaurants. Don’s Prime is a must for steak; La Fontaine’s breakfast will set you up for the day’s adventures.

It dawns on me that, although fractured, Route 66 still serves part of its original purpose. It will get you, broadly, from one side of the country to the other, but its beauty stems from the fact that you should, and often have to, leave it, to take in a landmark or a town and then rejoin it. Today’s Route 66 isn’t a strict path, it’s a guide that passes by some of the US’s greatest sights.

The final descent into the clutches of the Pacific takes me through Roy’s Motel & Café, Amboy — which is slowly being restored to former glory — to Barstow and to the Wigwam Motel in San Bernardino. From there it’s a straight line to Santa Monica, where the route officially finishes. I celebrate in the Pendry West Hollywood with palm tree-skimming, hazy views of Downtown LA.

The vast, urban sprawl is a world away from the twisty trials of Oatman and it must have been as overwhelming back then as it is right now.

Elegant Resorts can organised a 12-night itinerary from £3,949 per person with nights at the hotels above, plus The View Hotel in Monument Valley, Arizona, and Shutters on the Beach in Santa Monica.

The price also includes return flights with American Airlines, UK lounge access and car hire.