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Explore the World With Us, One Road Trip At A Time
Celebrate the 100th Anniversary of Route 66 (1926–2026) with Gearhead Getaways on the ultimate American road trip! This hosted journey takes you from the Chicago area to the Santa Monica Pier in true Mother Road style—packed with iconic Route 66 landmarks, classic roadside photo ops, historic lodging, and unforgettable small-town charm. We’ll keep the driving days comfortable so you can enjoy the adventure without feeling rushed. Our travel services ensure you have everything you need for a memorable experience.
Included in the trip are 11 nights of hotel accommodations, 3 dinners (welcome reception, halfway dinner, and farewell celebration), and attractions outlined in the itinerary.
From neon signs and diners to legendary attractions like Cadillac Ranch, Petrified Forest, and the famous “End of the Trail,” this is more than a trip—it’s a rolling celebration of America’s most famous highway. Spots are limited, so grab yours and let’s hit the road for an unforgettable adventure! 🛣️🚘✨
Join us for the Route 66 Road Trip!
October 4 - 15, 2026
Chicago, IL
October 4
We kick things off near Chicago with a welcome night in Burr Ridge, then hit the road at the iconic Route 66 “Begin” sign to start our 100th Anniversary adventure! 🏁🚗
Lodging: Hampton Inn Burr Ridge
Springfield, IL
October 5
We leave Chicago and hit the official Route 66 starting point, then roll through iconic roadside towns like Pontiac for Route 66 history and photo ops before arriving in Springfield, IL—home of classic diners, vintage vibes, and Lincoln landmarks. 🛣️🏁📸
Lodging: Route 66 Hotel
St. Louis, MO
October 6
St. Louis offers plenty for car enthusiasts. Snap a Corvette photo at the iconic Gateway Arch, then explore the National Museum of Transportation, featuring rare classics and historic vehicles. A drive across the old Chain of Rocks Bridge connects you to Route 66 nostalgia, while great food and riverfront views make this stop a highlight on the road.
Lodging: The Cheshire
Springfield, MO
October 7
Springfield is where Route 66 was officially named in 1926, earning it the title “Birthplace of Route 66.”
Today, travelers can enjoy its nostalgic diners, vintage motels, and landmarks celebrating the Mother Road’s rich history.
Lodging: Route 66 Rail Haven
Tulsa, OK
October 8
The drive to Tulsa takes you into the rolling hills and scenic beauty of northeast Oklahoma.
Along the way, you’ll experience wide-open highways, charming small towns, and a taste of true Americana before arriving in Tulsa—known for its warm hospitality, route 66 heritage, and entertainment.
Lodging: The Campbell Hotel on Rt 66
Amarillo, TX
October 9
Amarillo is pure Route 66 fun—snap the ultimate pics at Cadillac Ranch, then cap the night with a hosted group dinner at the legendary Big Texan, where the steaks are huge and the memories even bigger. 🛻🎨🥩🔥
Lodging: The Big Texan
Santa Fe, NM
October 10
Santa Fe is where Route 66 meets Southwest magic—stroll the historic Plaza, soak up the adobe charm, and enjoy the vibrant art and culture that make this stop unforgettable (plus plenty of iconic photo ops along the Mother Road). 🌵🏜️📸✨
Lodging: La Fonda on the Plaza
Gallup, NM
October 11
Gallup is classic Route 66 with a Southwest twist—along the way we’ll catch neon and roadside sights, then roll into town for trading posts, Route 66 history, and a stay at the legendary El Rancho Hotel, famous for its old Hollywood charm. 🌵🛣️✨
Lodging: Hotel El Rancho
Winslow, AZ
October 12
Winslow is a Route 66 bucket-list stop—grab the perfect photo at Standin’ on the Corner, soak up the charm of La Posada, and enjoy the nostalgic small-town vibes that make this stretch of the Mother Road unforgettable. 🎸🛣️📸✨
Lodging: La Posada Hotel
Kingman, AZ
October 13
Kingman is classic Route 66 fun—after rolling through iconic stops like Seligman and the scenic roads near Oatman, we’ll land in one of the most historic Mother Road towns for neon nights, diner vibes, and a stay at the Ramblin’ Rose. 🛣️✨🐴
Lodging: Ramblin Rose
Santa Monica, CA
October 14
Santa Monica is the grand finale—cruise the last stretch of Route 66 and finish at the legendary Santa Monica Pier “End of the Trail” sign, then celebrate with a hosted group dinner on the pier and an overnight stay at The Pierside Santa Monica. 🌊🏁🍔✨
Lodging: The Pierside Santa Monica