The Original - Route 66 Road Trip!!
Discover the Magic of Route 66
We drove Route 66 in the Spring of 2024, it had been a long-time dream to pick up the Mustang convertible and head out on the open road. We have listed some of the highlights in the details below, but to be honest it really is the Road Trip that has the most personalisation!
Whether you have time to do it all in one go, want to add on stays in towns and cities just off the route, travel by Motorbike or Convertible, we can tailor the journey for you, with a fair dose of experience!
We added on a detour to Monument Valley & did a Hot Air Balloon ride at dawn in Albuquerque for example.
The adventure begins in Chicago, a city buzzing with energy, deep‑dish pizza, and blues music. Wander through Millennium Park, snap a photo at “The Bean,” and fuel up with a classic breakfast at Lou Mitchell’s, a Route 66 institution since 1923. As you roll out of the city, the iconic “Begin Route 66” sign marks the start of your journey west.
Your first stretch takes you through the heart of Illinois, where small towns preserve the charm of mid‑century America. Stop in Joliet to visit the Route 66 Museum, a treasure trove of vintage signs, classic cars, and stories from the road’s golden era. In Pontiac, the Route 66 Hall of Fame & Museum offers murals, memorabilia, and the famous “Wall of Cars” , a perfect photo op. Spend the night at the Route 66 Hotel and Conference Centre in Springfield, decorated with retro flair and classic diner vibes.
Crossing into Missouri, the road winds toward St. Louis, where the shimmering Gateway Arch rises above the Mississippi River. Take a tram ride to the top for sweeping views, then enjoy barbecue at Pappy’s Smokehouse, a local legend. For a stylish stay, check into the Chase Park Plaza, a historic hotel overlooking Forest Park. As you continue west, stop in Cuba, Missouri, known as “Mural City,” where colourful street art celebrates the history of Route 66.
Next comes Meramec Caverns, a spectacular underground world once used as a hideout by the outlaw Jesse James. Guided tours lead you through cathedral‑like chambers and shimmering mineral formations. Just down the road, the quirky Uranus Fudge Factory offers humour, souvenirs, and, yes, delicious fudge.
Your journey continues into Oklahoma, home to some of the best‑preserved stretches of the Mother Road. In Tulsa, stay at the Campbell Hotel, a beautifully restored 1920s boutique property. Explore the Route 66 Historical Village, where vintage locomotives and oil derricks tell the story of Oklahoma’s boom years. In Oklahoma City, the National Cowboy & Western Heritage Museum brings the Old West to life with art, artifacts, and immersive exhibits. Don’t miss dinner at Cattlemen’s Steakhouse, a Route 66 classic serving hearty meals since 1910.
As you cross into Texas, the landscape opens into wide plains and big skies. In Amarillo, the legendary Big Texan Steak Ranch challenges hungry travellers to finish a 72‑ounce steak, free if you can conquer it. Even if you skip the challenge, the atmosphere alone is worth the stop. Spend the night on site at the Motel! Just outside town, the Cadillac Ranch art installation invites you to spray‑paint your mark on a row of half‑buried Cadillacs, a Route 66 rite of passage.
New Mexico greets you with desert landscapes, adobe architecture, and rich cultural heritage. In Tucumcari, neon signs glow at the Blue Swallow Motel, a beautifully preserved 1940s motor court where each room has its own garage. In Santa Fe, explore the Georgia O’Keeffe Museum, stroll through the historic plaza, and savour green‑chilli dishes at The Shed. Albuquerque’s Old Town offers charming shops and galleries, while the 66 Diner serves milkshakes and burgers in full retro style.
Crossing into Arizona, the scenery becomes dramatic and rugged. Stop in Holbrook to sleep in a concrete tipi at the iconic Wigwam Motel, one of the most photographed stops on Route 66. Nearby, the Petrified Forest National Park and Painted Desert offer surreal landscapes of fossilized wood and colourful Badlands. In Flagstaff, stay at the Weatherford Hotel, a historic landmark with frontier charm. From here, it’s an easy detour to the Grand Canyon, one of the world’s great natural wonders.
Further west, the old mining town of Kingman hosts the excellent Route 66 Museum, where exhibits trace the road’s evolution from wagon trails to modern highway. Continue to Oatman, a quirky Wild West town where burros (Donkey) roam the streets and gunfight reenactments entertain visitors.
Finally, you cross into California, where the Mojave Desert stretches endlessly toward the Pacific. Stop in Barstow at the Route 66 Mother Road Museum, then continue through Victorville and San Bernardino, home of the original McDonald’s site, now a museum of fast‑food history. As you reach Santa Monica, the ocean breeze greets you and the “End of the Trail” sign marks the triumphant finish of your journey. Celebrate with a stay at the Shore Hotel, overlooking the beach, and toast your adventure with cocktails on the pier.
Route 66 isn’t just a road, it’s a time capsule, a cultural icon, and the ultimate American adventure. Whether you’re chasing neon lights, roadside diners, or the freedom of the open highway, this legendary route promises a journey you’ll never forget
We truly love creating bespoke road trips and enjoy nothing more than discussing all options with you before pulling it all together in your own personalised itinerary!
It’s so easy to get started, simply give us a call, click on the enquiry button or book a consultation to design your dream trip!
