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Route 66 mural on wall in Pontiac, Illinois, USA

Driving Route 66

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By Beth Ellison


Route 66 is an American icon that for over sixty years spanned eight states, three time zones and nearly four thousand kilometres. Nowadays, travellers can take on the world’s most famous road trip by following the trail of the old road, which connects Chicago and Los Angeles.

In contrast to the fame of the route itself, the sights and experiences that can be taken in along the route remain largely under the radar of most travellers. This means that it can be hard to know where to start when planning your own trip. To help you plan your once in a lifetime Route 66 adventure, we've put together a list of the best stops to make sure you get your fill of the weird and wonderful places that make this one of the most unique and fascinating journeys in the world.

2026 marks Route 66's Centennial - celebrating 100 years of this iconic drive!

Starting in Chicago, the perfect song to kick off your American road trip is Frank Sinatra – My Kind of Town. Check out the list below for more road trip playlist suggestions!

Springfield, Illinois

The first stop when driving Route 66 is Springfield, Illinois. The main draw to Springfield is its affiliation with the late former president Abraham Lincoln, who served as leader during the American Civil War period. The town is where Lincoln lived and worked for seventeen years, prior to being elected as president. His former home is now a museum, and visitors are welcome at the Oak Ridge Cemetery, where in the summer months they can enjoy theatrical reeanactments at Lincoln's Tomb performed by actors in traditional Civil War period dress. Other historic sites include the Illinois State Capitol, the Lincoln Presidential Museum and a gold bust of the president that is said to bring good luck if you rub its nose.


Nearby you will also find ‘Brick 66’; a 2.5 kilometre stretch of hand-laid brick road that is sandwiched between vast green fields. Travelling along this restored stretch of narrow highway is a must for those who want to step into the past, and experience driving the authentic Route 66.


Playlist suggestion: Fleetwood Mac – Go Your Own Way


 

Civil war museum in Springfield, USA

The City Museum in St. Louis, Missouri

When you think of St. Louis you might think of it as a city best known for its giant arch, history and strong affiliation with blues music. This wouldn’t be wrong; however, after you visit the City Museum you are unlikely to remember it for anything else.


It’s worth stating from the outset, that to call this attraction a museum is a stretch of the word’s meaning. If you are hoping to find priceless artefacts or paintings here, you might be disappointed when you are met with a jungle of slides, mazes, ball pits and old aeroplanes propped up at roof level by a network of cranes and iron rod passages. Whilst this understandably might not be everyone’s idea of an afternoon well spent, for those fun-seekers amongst us this really can’t be missed, and it makes for an interesting stop when driving Route 66.


Playlist suggestion: Fontella Bass – Rescue Me


 

The arch in St Louis Missouri, USA, on Route 66

Amarillo, Texas

This northern Texan town of Tony Christie fame is the wild-west at its best. Whilst it's the only time you will stop in the mighty state of Texas on the route, the host of ranches on its doorstep and an infamous steakhouse ensures that Amarillo doesn’t disappoint and makes it a highlight of driving Route 66.


The Big Texan Steak Ranch & Brewery is legendary, and is more like a small theme park than a restaurant. During a visit here you can enjoy some typical rodeo amusements before sitting down to indulge in some classic Texan grub, washed down by a tower of beer or bottomless sodas. If you're brave enough, you can even try and eat for free here by opting to take part in the well-known food challenge that sees participants attempt to devour a 72 ounce steak, plus sides, in under an hour. After you've had your fill of the grill, you can end your night in style by being chauffeured back to your accommodation or campsite in a bull-horn fronted limo, driven by a stetson clad Texan.


On your way out of town, you will also have the chance to make a stop at the Cadillac Ranch. Here you will find a car graveyard, where a series of Cadillacs have been impaled into the ground, boot in the air, and spray painted. The scenes here have become classic material for Route 66 postcards, and are the perfect post-breakfast stop, before hitting the road again.


Playlist suggestion: Tony Christie – (Is This The Way To) Amarillo


 

Cowboys in Amarillo, Texas

Santa Fe, New Mexico

Santa Fe is a state capital unlike most others in the States. With a population of just under seventy thousand, it feels more like a large town than a city. But more than this, the Pueblo-style architecture and the dense mixture of Latin and Hispanic locals makes the city feel more diverse, vibrant and unique than perhaps any other town in America. Being so diverse, you can find some of the best Mexican eateries the region has to offer here too, as well as a thriving art scene, with galleries appearing on most corners.


If that's not enough to convince you to visit, just down the road you will also find the infamous town of Madrid, an old mining village and ghost-town that has come back from the dead in a big way. The village, that has become a popular place to settle for nomads, artists and craft makers, is now thriving and is one of the most memorable places to spend an afternoon when driving Route 66.


Playlist suggestion: Bob Dylan – Mr Tambourine Man


 

Alamo architecture in Santa Fe, USA

Petrified Forest, Arizona

As you wind your way through Middle America towards the West Coast, you'll come across a generous amount of woodland and forests. However, none will be quite the same as the Petrified Forest National Park. The trees that occupy this particular landscape haven’t flourished in quite some time, starting their life a mere two-hundred million years ago. Since then they have become fossilised and are posed like hundreds of fallen stone columns, covering a large site that is reminiscent of a scene from a post-apocalyptic movie. You can also find other ancient relics here, with impressively preserved rock paintings and carvings visible throughout the park. These historical wonders, coupled with their dramatic backdrop that comes in the form of the breathtaking Arizona desert, make this a stop worthy of a place on any Route 66 itinerary.


Playlist suggestion: David Bowie – Life on Mars


 

Route 66 going through the Petrified Forest in Arizona

Grand Canyon, Arizona

The Grand Canyon is a stop on Route 66 that needs little introduction. As one of the world’s true bucket-list destinations and a titan in tourism, it is one of the few places on earth that effortlessly exceeds its impressive reputation. The awe-inspiring views to be experienced here, as you watch the first light of the day breach the colossal canyon ceiling at sunrise, cannot be overlooked on any adventure through this part of The States. The best place to experience the Grand Canyon is at its South Rim, which is also home to the Grand Canyon Village and an informative Visitor Centre.


Playlist suggestion: America the Beautiful – Ray Charles


 

Famous Grand Canyon on a beautiful sunny day with blue sky in summer, Grand Canyon National Park, Arizona, USA

Las Vegas, Nevada

Whilst Las Vegas is not technically on Route 66, it is definitely a detour worth making! Much like the Grand Canyon, little introduction is needed for this icon. Whether your interests sway toward the casino floor, the famous nightlife or the world class food scene, Vegas has something for everyone, and catching the bright lights of the strip is a once in a lifetime experience not to be skipped.


Playlist suggestion: Viva Las Vegas – Elvis


 

Welcome to Fabulous Las Vegas sign, USA

Santa Monica Pier in Los Angeles, California

When it comes to Route 66, Santa Monica Pier marks the end of the road in quite a literal way. The pier, as it drops off into the Pacific Ocean, marks the official end of the route and with the classic Californian coast book-ending the scene, the Hollywood hills in the background, and the ocean as far as the eye stretches in front of you, it’s hard to imagine a more idyllic place to wrap up America’s most epic adventure.


Playlist suggestion: Boyz II Men – End of the Road


 

Route 66 end of the road sign in Santa Monica, California

To drive Route 66 yourself, take a look at our Route 66 - The Mother Road itinerary. Or for further inspiration, visit our USA Fly Drive Holidays pages.

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Written by Beth Ellison

Beth is a Procurement Manager for South East Asia in our Product Department in Kensington. Beth has worked at Trailfinders since 2016 and has travelled to 31 countries. Her favourite destinations include Namibia, the Galapagos Islands and Thailand.

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