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Route 66, affectionately called the “Mother Road,” is more than just a highway—it’s an emblem of American freedom, resilience, and nostalgia. Spanning from Chicago to Santa Monica, this historic route has inspired countless travelers and served as the backdrop for iconic movies like Cars, The Grapes of Wrath, and Rain Man. Along the way, classic diners, vintage motels, and roadside attractions transport visitors to a bygone era.
This itinerary takes you on a cinematic journey along Route 66, highlighting locations tied to these films and the landmarks that make the route legendary.
Day 1-2: Chicago, Illinois
Starting point of Route 66
Begin your journey in Chicago, the official starting point of Route 66. While the city itself isn’t prominently featured in our movies, its vibrant culture sets the stage for an unforgettable road trip.
- must-visit spots:
- Route 66 Start Sign (Adams Street): Snap a photo to commemorate the beginning of your adventure.
- Lou Mitchell’s Diner: A classic breakfast spot that has served travelers since 1923.
- movie connection: The Grapes of Wrath begins with the Joad family’s decision to leave their drought-stricken farm, mirroring the sense of embarking on a journey for a better future.
Day 3-4: St. Louis, Missouri
Gateway to the west
Cross the Mississippi River into St. Louis, where Route 66 begins to take on its iconic identity.
- must-visit spots:
- Gateway Arch: Symbolizing westward expansion, this landmark offers panoramic views of the city and the river.
- Ted Drewes Frozen Custard: A Route 66 classic serving frozen treats since the 1920s.
- movie connection: The sense of resilience and movement in The Grapes of Wrath aligns with the pioneering spirit celebrated here.
Day 5-6: Tulsa, Oklahoma
Echoes of americana
Oklahoma is rich with Route 66 nostalgia, offering classic roadside attractions and friendly small-town vibes.
- must-visit spots:
- Blue Whale of Catoosa: A whimsical, larger-than-life roadside attraction perfect for photos.
- Route 66 Vintage Iron Motorcycle Museum: Dive into Americana history with an extensive collection of classic motorcycles.
- movie connection: The rural landscapes here evoke scenes from The Grapes of Wrath, capturing the hardships and hope of Depression-era America.
Day 7-8: Amarillo, Texas
Deserts and diners
The Texas stretch of Route 66 offers wide-open spaces and quirky attractions that have become part of cinematic lore.
- must-visit spots:
- Cadillac Ranch: An art installation featuring half-buried Cadillacs, perfect for snapping colorful photos.
- The Big Texan Steak Ranch: A kitschy steakhouse offering a 72-ounce steak challenge for the bold.
- movie connection: The desert vibes in this region bring to mind the animated landscapes of Cars, a love letter to Route 66 and small-town America.
Day 9-10: Santa Fe, New Mexico
Southwestern charm
Detour slightly to Santa Fe, a historic and artsy city offering a mix of Route 66 history and Southwestern culture.
- must-visit spots:
- Santa Fe Plaza: Explore local shops and enjoy authentic Southwestern cuisine.
- La Fonda on the Plaza: A historic hotel that dates back to the 1600s, perfect for an overnight stay.
- movie connection: The sun-soaked landscapes of New Mexico add to the warm nostalgia of Cars.
Day 11-12: Flagstaff, Arizona
red rocks and retro motels
Arizona’s Route 66 stretch is packed with vintage motels and natural wonders.
- must-visit spots:
- Meteor Crater: A massive impact site offering guided tours and stunning views.
- Wigwam Motel: Stay in a classic Route 66 motel where rooms are shaped like teepees.
- movie connection: The retro motels and diners recall scenes from Cars, while the dramatic desert landscapes tie into Rain Man’s journey westward.
Day 13-14: Santa Monica, California
The end of the road
Finish your journey at the Santa Monica Pier, the western terminus of Route 66. The pier’s vibrant atmosphere and ocean views are a fitting finale to your cinematic adventure.
- must-visit spots:
- Route 66 End Sign: Mark the end of your journey with a commemorative photo.
- Santa Monica Pier: Enjoy the Ferris wheel, carnival games, and ocean breezes.
- movie connection: In Rain Man, Santa Monica represents the culmination of a transformative road trip, just as it does for Route 66 travelers.
Classic diners and motels along the way
- Delgadillo’s Snow Cap Drive-In (Seligman, Arizona): A quirky diner serving burgers and milkshakes with a side of humor.
- The Blue Swallow Motel (Tucumcari, New Mexico): A meticulously preserved 1940s motel with neon charm.
Practical tips for the trip
- length of trip: Allow at least two weeks to fully enjoy the experience.
- transportation: A classic car rental adds to the nostalgic feel, but any vehicle will do.
- essentials: Pack a camera, a Route 66 guidebook, and your favorite road trip playlist
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