My introduction to Route 66 was a little extreme. A few years ago, I was approached to assist with the travel arrangements for an unusual group. The idea was to take 66 classic and vintage Jaguar cars from the UK to America to drive the famous Route 66 from Chicago to Los Angeles. It was quite an undertaking for all involved. The logistics aren’t really the story, but I can confirm that 66 classic Jaguars did indeed make it to America, and most of them also completed the whole 2448 miles before returning home. I mention this tale not to highlight my involvement in this amazing road trip, but more to show how Route 66 continues to intrigue and attract visitors from all around the world, nearly 100 years after it was established.
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There is just something about Route 66 that gets under your skin. Whether it’s the promise of wide-open roads, the nostalgia of neon-lit diners, or simply the idea of heading west into the unknown, the ‘Mother Road’ has long held a special place in people’s hearts.
Originally commissioned in 1926, Route 66 was one of the first highways in the US road network. It linked Chicago with Los Angeles and stretched over 2,400 miles across eight states. Back then, it wasn’t just about leisure; it was a vital lifeline for farmers, workers, and families heading west during the Dust Bowl and the Great Depression. Later, in the post-war years, it became the ultimate road trip, American style, with shiny cars, neon lights, big skies, and the wide-open road.
Over the decades, Route 66 cemented its status as a cultural icon. From John Steinbeck’s novel, The Grapes of Wrath, to Nat King Cole’s song ‘Get Your Kicks on Route 66’, it’s been immortalised in books, songs, films, and TV shows. Even though it was officially removed from the US Highway System in 1985, the road never really died, it simply shifted into legend. Today, much of the original route is still drivable, lovingly preserved by local communities and road trip devotees.
And now, in 2026, Route 66 hits a major milestone: its 100th anniversary. A full century since it first appeared on American maps, and it’s still drawing travellers from all over the world, Jaguar convoys included! To mark the centenary, towns and cities along the route are planning all sorts of celebrations: classic car parades, festivals, roadside parties, and historical exhibitions. It’s shaping up to be a fantastic year to make the journey.
So, whether you’re a first timer with Route 66 on your bucket list or a returning road warrior chasing that same thrill, now could be the perfect time to experience it. Let’s hit the road and explore this legendary route. We can take you state by state, along Route 66, introducing you to some of the highlights that you can see from Chicago to the Pacific Ocean.
Every great road trip has to start somewhere, and for Route 66, that somewhere is Chicago. Right in the heart of downtown, just off East Adams Street, between Wabash and Michigan Avenues, near the Art Institute, you’ll find the iconic “Begin Route 66” sign. This is an essential photo stop before setting off westward. The urban buzz of the Windy City might seem a world away from the deserts and wide-open landscapes that lie ahead, but there’s something fitting about starting a journey of Americana from such a bold and exciting place.
Just a few steps from the official starting point is Lou Mitchell’s Diner, a true Chicago institution and a Route 66 staple since 1923 (before Route 66 was established!). This no-nonsense, classic American diner is the perfect spot for a proper breakfast before hitting the road. From eggs any style to baskets of fresh doughnuts served with coffee, Lou’s has fuelled generations of travellers, presidents, celebrities, and ordinary road trippers alike. There’s a good reason it’s sometimes called ‘the first stop on the Mother Road’.
Leaving the city behind, the road begins to show its Midwestern roots, passing through small towns and farmland, each with its own story to tell. One of the real gems along the Illinois stretch is Pontiac, a small town with a big Route 66 spirit. The Route 66 Hall of Fame and Museum is a must-see, filled with vintage memorabilia, classic car displays, and fascinating stories of the people who kept the road alive after its official decommissioning. Outside the museum is the largest Route 66 shield mural in the world, a popular selfie spot and a sign that you’re truly in road trip country now.
But Pontiac doesn’t stop there. The town is covered in over 20 hand-painted murals, many of them themed around Route 66, music, and local history. You can easily spend a couple of hours just wandering the streets with a camera in hand, discovering each one. There’s also the Pontiac-Oakland Auto Museum nearby, which adds an extra layer of classic motoring nostalgia to your visit.
Before crossing into the next state, it’s worth a brief detour to Wilmington, home of the famous Gemini Giant. Standing tall beside the Launching Pad Drive-In, this towering green spaceman is one of the original “Muffler Men” and an enduring symbol of classic roadside Americana. It’s one of those wonderfully oddball stops that makes Route 66 so endlessly entertaining.
Illinois might only make up the first 300 or so miles of Route 66, but it packs in a wealth of history, charm, and photo-worthy sights. From the skyscrapers of Chicago to the small-town charm of Pontiac and beyond, Illinois sets the tone beautifully.
| Route 66 Centenary Events in Illinois | Location | Date |
|---|---|---|
| Pontiac Car Show | Pontiac, Illinois | 20th September 2026 |
| International Mother Route Festival | Springfield, Illinois | 26th – 28th September 2026 |
In Missouri, Route 66 begins to roll through the green heart of the Midwest. The flat prairies of Illinois give way to gentle hills, winding rivers, and the beginning of the Ozarks. This stretch of the road is packed with small towns, vintage motor courts, and quirky roadside attractions, but it’s also where the route starts to feel a bit more adventurous.
First up is St. Louis, one of the biggest cities on the route and a major gateway to the west. While the modern road network has changed the original layout of Route 66 through the city, much of the historic path still weaves through neighbourhoods like Midtown and Maplewood. There’s plenty of charm to be found in the old diners, neon motel signs, and the distinct architecture from the heyday of mid-century travel.
One of the most unique features of the route here is the Chain of Rocks Bridge, which once carried Route 66 traffic across the mighty Mississippi River. Built in 1929, this mile-long bridge is famous for its 22-degree bend in the middle, a quirk of engineering that makes it unique. Although it’s now closed to vehicles, the bridge is open to cyclists and pedestrians, and walking across it offers a brilliant view of the river and a tangible sense of early Route 66.
Heading southwest, Route 66 snakes into the Missouri countryside, where forests close in a little and the road begins to climb and dip. This is cave country and nowhere makes that clearer than the spectacular Meramec Caverns, just outside the town of Stanton. A favourite stop since the 1930s, these enormous limestone caves are filled with stalactites, stalagmites, and dramatic underground formations. But what really sets them apart is the showmanship. Early Route 66 travellers were lured in by eye-catching billboards (which famously claimed the caverns were a hideout for Jesse James), and inside, the caverns still feature colourful lighting, music shows, and old-school Americana charm.
As you continue through the state, you’ll find plenty more classic sights. Towns like Cuba, known for its series of Route 66 murals, and Rolla, home to the Totem Pole Trading Post, keep the spirit alive with friendly welcomes and photo-worthy stops. Near Carthage, don’t miss the 66 Drive-In Theatre, a beautifully preserved, still-operational outdoor cinema that captures the golden age of road trip entertainment. If your timing’s right, you can catch a film under the stars, just like they did in the 1950s.
Missouri might only be the second state on the journey, but it’s often where Route 66 really starts to feel like an adventure.
| Route 66 Centenary Events in Missouri | Location | Date |
|---|---|---|
| Route 66 Centennial Kick-Off | Springfield, Missouri | 30th April – 2nd May 2026 |
| Route 66 Cars & Guitars Festival | Kirkwood, Missouri | 7th June 2026 |
| Birthplace of Route 66 Festival | Springfield, Missouri | 8th – 9th August 2026 |
At just 13 miles long, the Kansas section of Route 66 is the shortest of all the eight states. Blink and you might miss it, but that would be a real shame. This short stretch, tucked into the state’s southeastern corner, is absolutely packed with history, nostalgia, and small-town Americana. In many ways, it’s Route 66 distilled into its purest form: humble, authentic, and proud of its place in the story.
The first town that you’ll reach is Galena, a former mining town with a strong Route 66 identity and a surprising claim to fame. Here you’ll find the wonderfully restored Kan-O-Tex Service Station, now operating as ‘Cars on the Route’. The garage itself is a great example of early 20th-century roadside architecture, but what really draws visitors is the old tow truck parked outside. A rusted, big-eyed beauty, it apparently inspired the character ‘Mater’ in Pixar’s Movie ‘Cars’. It’s a playful, family-friendly stop, and a reminder of how Route 66 continues to create pop culture even today.
From Galena, the road meanders through the countryside to Riverton, home to Eisler Brothers Old Riverton Store, a genuine Route 66 survivor that’s been in business since 1925. It’s part general store, part café, and part time capsule. You can grab a sandwich, browse shelves lined with Route 66 memorabilia, and chat with locals who are only too happy to share stories about the road.
Just a little further along is one of Kansas’s most iconic landmarks, the Rainbow Bridge, officially known as the Brush Creek Bridge. Built in 1923, it’s the only remaining Marsh Arch bridge on the entire route, a graceful concrete structure with elegant lines that has become one of the most photographed sites on Route 66. You can still drive across it or stop for a quiet moment and take in its simple beauty. It’s not flashy, but it’s a true symbol of early American roadbuilding and the spirit of the route.
Kansas doesn’t have the flashy attractions of some other states; no neon cowboy signs, giant fibreglass mascots, or sprawling motels. But what it offers instead is sincerity. The people here are passionate about preserving their stretch of the road, and you can feel that pride in every mural, restored filling station, and hand-painted sign.
| Route 66 Centenary Events | Location | Date |
|---|---|---|
| The Drive Home | Santa Monica to Chicago | 3rd – 12th January 2026 |
| The Great Race (Vintage Cars) | Chicago to Santa Monica | 20th – 28th June 2026 |
Stretching across more than 400 miles, Oklahoma boasts one of the longest and most authentic stretches of Route 66. If you want to feel what driving the Mother Road was really like back in its heyday, then this is the place to do it. With red earth, open skies, and a mix of roadside kitsch and cowboy culture, Oklahoma feels like the point where East truly begins to meet West.
One of the most beloved stops in the state is the Blue Whale of Catoosa, just outside Tulsa. Built in the early 1970s as a gift from a local man to his wife, this giant, smiling blue whale sits beside a small pond and was originally part of a swimming pool. Although it’s no longer open for diving and splashing around, it’s been beautifully restored and remains a classic photo stop. It’s delightfully odd, completely charming, and exactly the kind of thing that makes Route 66 so endearing.
As you continue west through Oklahoma, the route weaves through a string of small towns, each offering a slice of Americana; vintage gas stations, neon signs, classic diners, and the sort of people who wave as you drive past. Eventually, you’ll roll into Oklahoma City, the state capital and a great place to stretch your legs and dig into the region’s heritage. A standout stop here is the National Cowboy & Western Heritage Museum, which offers a fascinating look at the history of the American West. From Native American culture and cowboy gear to Western art and film, it’s a rich and engaging collection that adds real depth to your journey. It’s not strictly Route 66-focused, but it fits the theme of westward exploration perfectly.
Further down the road, in the town of Clinton, you’ll find the Oklahoma Route 66 Museum, an absolute must for anyone following the route. This well-curated museum walks you through each era of Route 66 history, complete with vintage cars, recreated shop fronts, and the sounds of 1950s jukeboxes playing in the background. It’s informative without being stuffy, and ideal for picking up some context before heading deeper into the western states.
Other highlights in Oklahoma include the Arcadia Round Barn, a beautifully restored circular barn that’s become a Route 66 icon, and Pops, a modern roadside diner and fuel stop with a towering neon soda bottle out front and hundreds of fizzy drinks lining the shelves inside.
Oklahoma is where the road starts to feel timeless, part vintage postcard, part living history. It’s the kind of place where you find yourself slowing down, not because you have to, but because you want to. And that’s what Route 66 is all about.
| Route 66 Centenary Events in Oklahoma | Location | Date |
|---|---|---|
| Classics Around The Barn | Arcadia, Oklahoma | 12th April 2026 |
| Route 66 Road Fest | Tulsa, Oklahoma | 21st – 22nd June 2026 |
| Route 66 Centennial Car Show | Sapulpa, Oklahoma | 18th August 2026 |
Route 66 Holidays by Freedom Destinations
Chicago | St. Louis | Springfield | Oklahoma City | Amarillo | Albuquerque | Grand Canyon | Las Vegas | Los Angeles
Chicago | Springfield | Tulsa | Oklahoma | Albuquerque | Amarillo | Santa Fe | Grand Canyon | Las Vegas | Los Angeles
Chicago | Springfield | Tulsa | Clinton | Amarillo | Santa Fe | Gallup | Flagstaff | Williams | Laughlin | Victorville | Los Angeles
Chicago | St. Louis | Springfield | Oklahoma City | Amarillo | Albuquerque | Grand Canyon | Las Vegas | Los Angeles
Chicago | Springfield | Tulsa | Oklahoma | Albuquerque | Amarillo | Santa Fe | Grand Canyon | Las Vegas | Los Angeles
Chicago | Springfield | Tulsa | Clinton | Amarillo | Santa Fe | Gallup | Flagstaff | Williams | Laughlin | Victorville | Los Angeles
By the time you reach Texas, Route 66 has truly settled into its stride. The landscape opens up into wide, flat plains, where the sky seems to stretch on forever and the horizon glows pink at sunset. Texas may only claim about 180 miles of the Mother Road, but as with most things in the Lone Star State, what it lacks in length it makes up for in sheer presence.
One of the most iconic stops along this stretch is the Midpoint Café in Adrian, which, as the name suggests, sits exactly halfway between Chicago and Santa Monica, at mile 1,139. This humble roadside diner has become a rite of passage for Route 66 travellers, with a big sign out front proudly declaring, “When you’re here, you’re halfway there!”. The café itself is a cosy, retro spot with homemade pies and a friendly atmosphere. There’s also a small gift shop next door, perfect for picking up a memento to mark your progress. It’s a simple but symbolic stop that makes you pause and reflect on just how far you’ve come.
A little further down the road, you’ll roll into Amarillo, the biggest city on the Texas stretch of Route 66, and home to two legendary attractions. First up is the Cadillac Ranch, a surreal and much-loved roadside art installation. Here, ten vintage Cadillacs are half-buried nose-first in a row in the dusty earth, their tail fins sticking up like outlandish tombstones. Over the years, they’ve been spray-painted by thousands of visitors, creating a constantly evolving, technicolour monument to the American car culture that helped make Route 66 famous. Cans of spray paint are often left behind by other travellers, so you can add your own mark to this collaborative piece of public art.
Don’t miss Amarillo’s Route 66 Historic District, a stretch of old brick road lined with antique shops, cafés, and vintage signage that echoes the golden age of American road trips.
After all that fresh air and creativity, you’ll want to refuel, and where better than the Big Texan Steak Ranch? Just off I-40 (which now overlaps much of the original route), this over-the-top steakhouse has been serving travellers since the 1960s. It’s famous for its 72oz steak challenge: eat it all, including sides, in under an hour, and it’s free. Whether you’re brave enough to try or just there for the spectacle, it’s a classic Route 66 experience.
Texas may be a short chapter in the Route 66 story, but it’s a vivid one, big on flavour, full of bold roadside icons, and steeped in the proud, independent spirit of the American Southwest.
| Route 66 Centenary Events in Texas | Location | Date |
|---|---|---|
| Dream Maker Station Car Show | Midpoint, Texas | 10th May 2026 |
| Texas Route 66 Festival | Statewide | 5th – 14th June 2026 |
New Mexico is where Route 66 takes on a noticeably different flavour. The landscapes become more dramatic, the colours warmer, and the cultural influences more diverse. This is where red rock cliffs meet turquoise skies, and adobe buildings sit side-by-side with glowing neon motel signs. It’s part Wild West, part Southwest mystique, and all unmistakably Route 66.
One of the most memorable stretches is through Albuquerque, the largest city on the route in New Mexico and a place where old meets new in all the right ways. The city has fully embraced its Route 66 heritage, especially along Central Avenue, where the Mother Road cuts right through town. Here you’ll find some of the best Route 66 neon signage still flickering to life each evening, from vintage motels and diners to refurbished theatres and petrol stations. It’s a visual feast and a nostalgic treat, especially after dark when the signs glow against the desert sky.
Not far from the route, Albuquerque’s Old Town offers a completely different vibe. Dating back to 1706, this historic district is all winding adobe alleyways, Spanish churches, and artisan shops. It’s a great place to slow things down, browse handmade jewellery and pottery, and soak in the deep roots of the region’s Native American and Hispanic cultures.
Further west, near the Arizona border, lies the town of Gallup, long a favourite stop for travellers, cowboys, and even Hollywood stars. The standout here is the El Rancho Hotel, an atmospheric slice of vintage glamour built in 1937. Known as “the hotel of the stars,” El Rancho hosted the likes of John Wayne, Humphrey Bogart, and Katharine Hepburn when they were filming Westerns nearby. With its rustic lobby, grand staircase, and rooms named after movie legends, it’s easy to imagine yourself in a bygone era. Even if you’re not staying the night, it’s well worth a visit for a drink, a bite to eat, or just to take in the cinematic charm.
Other New Mexico highlights include Santa Rosa, home to the Route 66 Auto Museum, packed with restored classic cars and chrome-drenched nostalgia, and Tucumcari, a small-town bursting with retro motels, vibrant murals, and more dazzling neon. The Blue Swallow Motel here is one of the most iconic stops on the entire route, beautifully preserved, lovingly operated, and lit up each night in brilliant blue and pink. New Mexico feels like the soul of Route 66, full of colour, character, and contrasts.
| Route 66 Centenary Events in New Mexico | Location | Date |
|---|---|---|
| Mothership On The Mother Road | Albuquerque, New Mexico | 17th May 2026 |
| Route 66 Summerfest | Albuquerque, New Mexico | 19th July 2026 |
If there’s one state that perfectly captures the spirit of Route 66, wide open roads, surreal landscapes, and kitschy roadside treasures, it’s Arizona. This is where the route winds through painted deserts, towering rock formations, and sleepy towns that still feel like the Wild West. Every stop seems to offer either a jaw-dropping view or a piece of pure Americana.
Let’s start in Winslow, a name that might ring a bell for any fans of the band The Eagles. The town proudly plays up its lyrical fame with the ‘Standin’ on the Corner Park’, a playful tribute to the line from “Take It Easy.” There’s a statue of a guitar-playing figure, a mural of a flatbed Ford, and, yes, a real flatbed Ford parked permanently nearby. It’s wonderfully tongue-in-cheek, and yet surprisingly moving in its simplicity. Travellers from around the world pause here for a photo and a moment of musical nostalgia.
Just outside Holbrook, you’ll find one of Arizona’s most unique natural wonders, the Petrified Forest National Park. Unlike anything else along the route, this otherworldly landscape is scattered with colourful, fossilised trees that date back over 200 million years. The park straddles Route 66 and even contains a stretch of the original roadbed, complete with remnants of old telephone poles. It’s one of the few national parks directly accessible from the route, and a must-visit for its sheer geological oddity and rugged beauty. The drive through the park takes you past sweeping desert views, petroglyphs, and rainbow-hued Badlands.
In Holbrook, don’t miss the chance to sleep in a concrete teepee at the Wigwam Motel, an iconic Route 66 stop since the 1950s. One of only three remaining Wigwam Villages in the U.S., it’s a rare chance to stay in a room shaped like a giant tipi, surrounded by classic cars parked out front. It’s kitsch, it’s charming, and it’s exactly the kind of quirky overnight stop Route 66 is famous for.
Further west, Flagstaff is a bustling mountain town with strong Route 66 heritage. It’s a good base for visiting the Grand Canyon (a slight detour to the north), but it also offers plenty of its own attractions, historic buildings, retro diners, and railway nostalgia.
As you near the California border, don’t miss Seligman, widely credited as the town that helped kick-start the Route 66 revival. Locals like Angel Delgadillo, the town barber, were instrumental in preserving the legacy of the road when it was bypassed by the interstate. Today, Seligman is a cheerful time capsule full of souvenir shops, restored storefronts, and classic American spirit.
Arizona’s stretch of Route 66 offers both natural wonders and playful retro charm in equal measure.
| Route 66 Centenary Events in Arizona | Location | Date |
|---|---|---|
| Gunslinger Car Show | Holbrook | 31st May 2026 |
| Route 66 Car Show | Williams | 6th – 7th June 2026 |
| Mother Road Classic Car Show | Flagstaff | 16th August 2026 |
Crossing into California, there’s a noticeable shift in the air. The desert is still vast and unforgiving, but there’s a sense of anticipation, the feeling that the journey is nearing its end, and the ocean isn’t far away. The California stretch of Route 66 is full of contrasts, empty Mojave landscapes, oddball roadside art, sun-baked ghost towns, and eventually, the sprawl of Los Angeles and the glitter of the Pacific.
One of the most memorable stops in the California desert is Elmer’s Bottle Tree Ranch, near Oro Grande. This eccentric forest of metal poles and colourful glass bottles was the work of Elmer Long, who began building it in the 2000s using bottles he’d collected with his father. The result is an otherworldly grove of bottle “trees” adorned with quirky signs, old typewriters, rusty tools, and all manner of found objects. The light catches the coloured glass in beautiful, unexpected ways, especially in the early morning or late afternoon. It’s whimsical, creative, and utterly Route 66.
Further west, the town of Barstow offers a glimpse into the route’s mid-century heyday. Stop by the Route 66 Mother Road Museum, housed in the old Harvey House train depot. It’s small but packed with artefacts and photos that capture the road’s evolution through California, especially as the area grew with post-war migration and car culture. Barstow’s vintage signs and old motels hint at its past as a major stopover for weary travellers heading west.
Another standout is Victorville, where you’ll find the California Route 66 Museum. It’s interactive, fun, and full of photo ops, you can pose on a vintage motorbike or sit in a 1950s diner booth. These museums along the route may vary in size and polish, but they all share a deep passion for preserving Route 66 history, and this one’s no exception.
As the route winds its way into Los Angeles, the sprawl and traffic of modern California take over. Much of the original road has been swallowed up by the city, but if you trace the route through Pasadena and Hollywood, you’ll spot occasional surviving landmarks, old theatres, classic diners, and neon signs that hint at the road’s storied past.
Eventually, Route 66 comes to its symbolic end at the Santa Monica Pier. While not the original terminus (that was once in downtown LA at the intersection of Broadway and 7th Street), the pier has become the recognised and celebrated end point of the Mother Road. There’s even a sign that reads “End of the Trail”, where countless travellers pose with windswept hair and big smiles after completing their cross-country pilgrimage.
Standing there, with the Pacific stretching out in front of you and 2,448 miles behind, it’s hard not to feel a bit emotional. Route 66 is more than just a road, it’s a living story of 20th-century America, told through diners and motels, bridges and gas stations, red rocks and blue neon. And finishing it here, where the land runs out, feels like the perfect ending.
| Route 66 Centenary Events in California | Location | Date |
|---|---|---|
| Route 66 Art Exhibition | Newport Beach, California | 5th May – 29th June 2026 |
As Route 66 approaches its 100th birthday in 2026, the world is once again turning its attention to this legendary stretch of tarmac. Towns and cities all along the route are preparing to celebrate the centenary in style, with special events, car rallies, festivals, parades, exhibitions, and live music planned throughout the year. From Chicago to Santa Monica, there’ll be no shortage of ways to honour the history, stories, and communities that have made the Mother Road so iconic.
It’s the perfect time to plan your own trip too. Whether you’re ticking off a lifelong dream, revisiting a favourite stretch, or simply curious to see what all the fuss is about. Driving Route 66 during its centenary year promises something truly unique: the chance to experience the road in celebration, surrounded by fellow travellers and enthusiasts from across the globe.
You don’t have to be in a classic Jaguar car for Freedom Destinations to help you fulfil your dream of travelling Route 66. Whether you choose a rental car, a motorhome or a motorcycle, Freedom’s America Travel Experts can create a Route 66 itinerary that makes the most of the Mother Road.
And that’s the magic of Route 66. It’s not just a road, it’s a storybook, a time machine, a celebration of movement and discovery. Whether you’re drawn by the nostalgia, the scenery, the roadside oddities, or the thrill of the quintessential American road trip, the journey always gives you more than you expect.
So, if you’ve ever thought about driving Route 66, 2026 is the year to do it. The bunting will be out, the classic cars will be polished, and the neon signs will be glowing just a little bit brighter. All that’s missing is you.
Richard has more than 25 years of experience working within the travel industry. He has travelled widely in the USA, Australia and Africa and enjoys exploring National Parks and other wilderness areas.
