I’ve lost count of how many road trips I’ve clocked up in the United States, but it’s a form of free-roaming travel adventure that remains an abiding personal passion. From navigating the mighty interstate highways to losing yourself on the forgotten backroads, where big skies, lonely landscapes and totems to the past are all part of the experience. But there’s one classic American touring route that holds the unique distinction of capturing the hearts and minds of tens of millions of international travellers, every year. Adding to its allure, 2026 marks its centenary. Yes, Route 66. The Mother Road. The Main Street of America.  

I’m just back from taking a fresh foray on the celebrated road, loading up on all my travel needs, including car rental and roadside stops, with Booking.com. The global travel leader has been named as the Official Travel Partner of the Route 66 Centennial, particularly given its one-stop-shop versatility in locking in all your travel bookings, from transport and attractions to accommodation. Interestingly, Booking.com’s 2026 Travel Predictions highlight that 73% of Kiwi travellers are drawn to road trips that allow them to meet new people. Route 66 delivers that in spades, particularly in the evocative smaller towns.  

Roadside attractions on Route 66. Photo / Supplied 

Stretching nearly 4000 kilometres from Chicago to Santa Monica, the historic cross-country route ribbons its way through eight states and fabled towns including Tulsa, Amarillo, Albuquerque, and Flagstaff, each offering authentic opportunities for connection on a great American road trip. Roadies give travellers what they want most: better value, the freedom to explore multiple destinations, and local experiences at your own pace. With thousands of accommodations, rental cars, and unique experiences available along the route, Booking.com is the go-to for unforgettable road trips, deeply threaded with the stories, landmarks, and people that make Route 66 so special. Throughout the year, most Route 66 roadside towns and cities are pulling out all the stops, with celebratory festivals and special events to accentuate the experience.  

You’d certainly need some serious stamina to knock-off the entire route from Chicago to Santa Monica. Those that do typically stretch the journey out over a month. But if you’re keen just to enjoy a signature slice of Route 66 Americana over the course of a week, there’s some great options. First, give the California road-trip on the remnants of Route 66 the wide berth. Traversing mostly desert, it’s interminably boring. But definitely fill your Insta-feed with some cheesy snaps in front of the end of the trail Route 66 sign on Santa Monica Pier if you happen to be in LA. 

End of the Trail at Santa Monica Pier. Photo / Mike Yardley

My favourite chunk of Route 66 is the Arizona section, which I explore in detail in a separate article. A close runner-up to that is the Illinois section, which spans 500km. It captures the essence of Route 66, replete with retro Americana delights. In Illinois, vast stretches of the original road have actually been preserved, so you can drive on the real deal, flanked by seemingly endless cornfields. A necklace of small towns drenched in neon soon beckon. Wilmington is first up, home to one of Mother Road’s most beloved Space Age landmarks, Gemini Giant. He’s a bright green thirty-foot-tall fibreglass spaceman, towering above the old Launching Pad Drive In diner. Nearby in Atlanta, you can see his mate, Tall Paul, another roadside colossus, clutching a hot dog. Call into Dwight and Odell, home to two little Texaco gas stations from the 1930s – classic canopied roadhouses studded with vintage bowsers.  

A show-stopper town is Pontiac, vividly bedecked in giant wall murals evoking Route 66’s glory days. Many of the murals were created by a local artist, Bob Waldmire, who binge-tripped the Mother Road in his VW Microbus, which was immortalised in the Cars movie as Fillmore. Pontiac’s sidewalks are studded with miniature classic cars as a salute to the great American models that regularly purred through. Springfield, Illinois is a hot spot for history buffs, like a living shrine to Abraham Lincoln. You’ve got the holy trinity of Honest Abe here – his home, his presidential library, and his tomb.  

Mike wedged in a classic car in Pontiac. Photo / Mike Yardley 

Don’t miss the Cozy Dog Drive-In in Springfield. The owner created the revered American corn dog. Have two of them. Just before you the Missouri state line beckons in Illinois, the last gasp is the Old Chain of Rocks Bridge. It was built to spirit Route 66ers across the Mississippi River. But it’s such an unusual bridge, because it’s a mile-long and has a 30-degree angled bend mid-way. This major design defect was the catalyst for countless crashes. Nowadays, this remarkable relic of Route 66 has been repurposed as one of the world’s longest cycling and pedestrian bridges. Stetch your legs and enjoy the stroll! 

Chain of Rocks Bridge on Route 66. Photo / Supplied 

Rediscover the spirit of the open road. Booking.com features thousands of accommodation options along Route 66, from nostalgic motels to retro-inspired stays. With access to thousands of car rental options, flexible booking features, free cancellation on many properties, and the ability to plan an entire trip in one place, Booking.com makes it easy to build a customised trip, on the website or user-friendly app.  

I flew to Los Angeles with Fiji Airways who have spread their wings with an extensive international network, including multiple American destinations. From New Zealand, fly to Nadi from Auckland, Wellington or Christchurch and enjoy seamless connections to the well-timed USA services. Fly your way with Fiji Airways with a flexible range of fares and add-ons, in Economy and Business class. If you fancy some extra comfort in Economy, opt for a Bula Space seat. 

Mike Yardley is Newstalk ZB’s resident traveller and can be heard every week on Jack Tame Saturday Mornings.