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Route 66 Centennial Cruise
There is no better year than 2026 to go on the classic American road trip celebrating the 100th anniversary of Route 66.
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Chicago, IL
Start your trip with a day exploring the Windy City, a city rich in culture. Begin your morning in Millennium Park to see the iconic “bean” sculpture, then head over to the river to get a boat tour of the city’s famous architecture. A trip to Chicago isn’t complete without tasting the staples, deep dish pizza, Chicago style hot dogs, and the comfort of a midwestern diner. To officially kick off the road trip stop by the “begin route 66 sign” and make sure to snap a picture.
Where to stay: Omni Chicago Hotel
What to see: Begin Route 66 sign
Where to eat: Lou Mitchell’s Diner
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Pit Stop
+Stop by the Historic Standard Oil Gas Station built in 1932 that welcomed travelers during the heyday of Route 66.
Location: Standard Oil of Illinois Gas Station, 400 S West St, Odell, IL 60460
Distance: 88 Miles
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St Louis, MO
Continue southwest until you reach St Louis, aptly known as the “Gateway to the West.” Visit the iconic Gateway Arch, the tallest manmade monument in the western hemisphere standing 630 feet tall. If you're a classic car fanatic, cruise around the St. Louis Car Museum to see the cars of your dreams. No visit to St. Louis is complete without Ted Drewes Frozen Custard, serving delicious custard since 1929, or Donut Drive-In, located just down the street.
Distance: 211 Miles
What to see: Gateway Arch
Where to eat: Drewes Frozen Custard or Donut Drive In
Pit Stop
+Enjoy a midwestern treasure, an authentic hot dog from Cozy Dog Drive In, serving travelers on Route 66 since 1949.
Location: Cozy Dog Drive In, 2935 S 6th St, Springfield, IL 62703
Distance: 166 Miles
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Springfield, MO
Springfield is famously known as the birthplace of Route 66 and a pivotal site for the Civil War. Visit the History Museum on the Square to prepare for the journey ahead and learn all about Route 66’s history. If you’re a history buff, explore Wilson’s Creek National Battlefield; this marks the spot of the first civil war battle fought west of the Mississippi River. Grab a bite at the cozy College Street Café before you continue on your way.
Distance: 310 Miles
What to see: Route 66 Car Museum
Where to eat: College Street Café
Pit Stop
+If you’re traveling with kids, stop in the town that inspired the character Mater in the movie Cars. The town has fully embraced the movie and even has “Cars” movie themed displays.
Location: Cars on the Route, 119 N Main St, Galena, KS 66739
Distance: 85 Miles
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Tulsa, OK
No other city celebrates the history of Route 66 like Tulsa, Oklahoma. Of course, visiting these iconic spots is necessary. Route 66 activities include the Route 66 Historical Village, Buck Atoms Cosmic Curios, and a picture with the Desert Hills Motel neon sign. Within Tulsa lies a massive 66.5-acre waterfront park that’s fun for all ages and offers hands-on activities, games and popup experiences. Before you leave, head downtown to visit some of Tulsa’s architectural treasures.
Distance: 110 Miles
What to see: Route 66 Neon Sign Park at night
Where to eat: Ike’s Chili
Pit Stop
+One of the newer landmarks on Route 66 is Pops 66 Soda Ranch which features a full-service restaurant, gas station, convenience store and more bottled soda options than you could ever imagine.
Location: Pops 66, 660 OK-66, Arcadia, OK 73007
Distance: 90 Miles
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Oklahoma City, OK
Offering a blend of western heritage and modern culture Oklahoma City is a true outdoor recreation, entertainment and culinary destination. Visit the National Cowboy & Western Heritage Museum, and if you’re lucky, catch an Oklahoma City Thunder game right next to Scissortail Park. Eat dinner at the famous Cattleman’s Steakhouse serving hungry cowboys, ranchers and travelers since 1910. After a good night’s rest, you will be ready to hit the road again.
Distance: 22 Miles
Where to stay: Omni Oklahoma City
What to see: National Cowboy & Western Heritage Museum
Where to eat: Cattleman’s Steakhouse
Pit Stop
+The beautiful art deco building housing the Tower Station and the U-Drop Inn Café is one of the most photographed Route 66 attractions; it began servicing travelers in 1936.
Location: U-Drop Inn Cafe, 105 E 12th St, Shamrock, TX 79079
Distance: 165 Miles
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Amarillo, TX
The drive from Oklahoma to Amarillo is packed full of Route 66 roadside fun, but once you reach Texas, fill your belly at the Big Texan Steak Ranch & Brewery. For the truly brave, attempt the famous 72-oz steak challenge. Walk off your meal and explore Amarillo’s historic Route 66 District, where you can visit unique shops, local restaurants and lively bars.
Distance: 94 Miles
What to see: Historic Route 66 District
Where to eat: Big Texan Steak Ranch & Brewery
Pit Stop
+Route 66 wouldn’t be complete without a stop at Cadillac Ranch.
Location: Cadillac Ranch, 13651 I-40 Frontage Rd, Amarillo, TX 79124
Distance: 10 Miles
Pit Stop
+Get a picture with the Route 66 midpoint sign and grab a bite at the Midpoint Café.
Location: Midpoint Cafe and Gift Shop, 305 Historic Rte 66, Adrian, TX 79001
Distance: 41 Miles
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Santa Fe or Albuquerque, NM
The choice is yours for your next stop. You can either drive to Santa Fe, the original Route 66 path, or travel through Albuquerque, the newer and more direct path. Santa Fe is a small, laid-back city known for its art scene. Meanwhile, Albuquerque is known for its lively downtown and cultural diversity. Wherever you land for the night, make sure to eat at a restaurant serving traditional New Mexican cuisine.
Distance: 229 Miles (Santa Fe), 238 Miles (Albuquerque)
What to see: Georgia O’Keefe Museum, Historic Old Town District
Where to eat: El Farol, Garduño's, Sawmill Market
Pit Stop
+Spend a night or stop for a picture at the Wigwan Motel, a historic Route 66 landmark that features 15 concrete teepee-shaped rooms complete with vintage cars on display.
Location: 811 W Hopi Dr, Holbrook, AZ 86025
Distance: 295 Miles from Santa Fe or 235 Miles from Albuquerque
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Flagstaff, AZ
Entering Flagstaff feels like a totally different world on Route 66. This quirky mountain town is the perfect mix between outdoor adventure and Route 66 nostalgia. Hit the trails in the surrounding areas or stroll down the original Route 66 path in downtown Flagstaff. At night head to Lowell Observatory to look through telescopes where Pluto was first discovered. Enjoy a meal at MartAnnes Burrito Palace before continuing your journey.
Distance: 90 Miles
What to see: Lowell Observatory
Where to eat: MartAnnes Burrito Palace, 112 E Rte 66, Flagstaff, AZ 86001
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Grand Canyon (detour)
Although not directly on Route 66, you cannot pass the opportunity to visit the breathtaking Grand Canyon. We promise this detour is well worth it. After a busy day exploring the national park, head to the Village Historic District for a trip back in time. Spend the night under a starry sky (by camping in style of course) and wake up to a majestic sunrise.
Distance: 80 Miles
What to see: Sunrise or sunset at Mather Point
Where to eat: Grand Canyon Village Historic District
Pit Stop
+ Stop in for a burger and homemade root beer float at Mr. D’z Route 66 Diner.
Location: Mr. D'z Route 66 Diner, 105 E Andy Devine Ave, Kingman, AZ 86401
Distance: 173 Miles
Pit Stop
+No matter the time, stop for a treat from The Donut Man which offers fresh donuts 24/7.
Location: The Donut Man, 915 E Rte 66, Glendora, CA 91741
Distance: 292 Miles
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Santa Monica, California
As you arrive in Santa Monica, bask in the cool coastal breeze marking the end of your Route 66 journey. Make sure to take a picture with the sign on the pier marking the end of your trip. Stretch your legs while exploring all the activities the pier has to offer. For a one-of-a-kind souvenir, stop by the Santa Monica Visitor Information Center for a complimentary Route 66 certificate of completion.
Distance: 45 Miles
Where to stay: Omni Los Angeles Hotel
What to see: End of the Trail Sign
Where to eat: Big Dean’s Oceanfront Café
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More Adventures to Enjoy
From sea to shining sea, America’s Hotel Company plays host to coastal escapes, desert drives, city breaks, and more. Hop in and hit the road.
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Midwestern Mileposts
Discover the heart of the Midwest on a road trip where iconic sports, regional flavors, and cultural landmarks define each spot.
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Blue Ridge Rhythm Route
Experience the best of the Southeast on a road trip from Nashville to Asheville, and Charlotte, where music, mountain scenery and Southern culture come together.
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