66 steps to the perfect Route 66 road trip

An updated take on the classic American road trip

There’s nothing quite like a classic road trip – a dog-eared map impossible to re-fold correctly, the rush of wind flowing through rolled-down windows and endless possibilities for adventure. Once the primary highway from America’s interior to the West Coast, the most quintessential U.S. road trip is Route 66, a 2,451 well-traveled road from Chicago, Ill. to Los Angeles, Calif.

Dubbed “The Mother Road” by John Steinbeck, Route 66 cuts a diagonal route through eight states: Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California. With so much to see along the way, from kitschy attractions to classic Americana to the world’s largest everything, here are 66 steps to the perfect Route 66 road trip.

Pre-trip

1. Before you go, read John Steinbeck’s classic “The Grapes of Wrath.” There’s an eclectic collection of curiosities to see along “The Mother Road,” which was immortalized in John Steinbeck’s classic.
2. Begin the trip in Chicago, Ill. Fly into Chicago O’Hare International Airport and save. With airfare to Chicago O’Hare down 41 percent compared with last year, this is the time to go.  
3. If you fly into Chicago, rent a car for your journey, and check out our tips for a worry-free road trip.
4. Take your time so you can support the mom-and-pop roadside motels, neon-lit diners and old-time soda fountains along the way.
5. Stop to take selfies at the old-school service stations along the route, many of which are closed.

Illinois

6. Take a photo in front of the world’s largest Route 66 shield and admire kitschy Route 66 memorabilia at the Route 66 Association of Illinois Hall of Fame and Museum.
7. Eat a cozy dog, similar to a corn dog, at the aptly named Cozy Dog Drive In, which has been open since 1949.
8. Grab a soda at Doc’s Soda Fountain. Originally a pharmacy built in the 1880s, the soda fountain was added to the business in the 1950s.
9. Pull over to see the world’s largest covered wagon in Lincoln, Ill. Located on the front lawn of the Best Western Lincoln Inn, near historic Route 66, the 24-foot tall Railsplitter Covered Wagon is recognized by the “Guinness Book of World Records“ as the largest covered wagon in the world.
10. You can’t roll through Collinsville, Ill. without stopping to snap a photo of The World’s Largest Catsup Bottle®, Built in 1949, the 170-foot-tall Brook’s Catsup Bottle was once a water tower.
11. Fill up for gas at Soulsby Service Station in Mount Olive, Ill., the oldest operational service station on the highway in Illinois.
12. Stop for provisions at Gray’s Gay Parita, a re-creation of a 1930s stone-faced filling station three miles west of Halltown, Ill.
13. Bunk at the five-room, Art Deco-Streamline Modern-style Boots Court Motel in Carthage, Ill.
14. Grab some chicken at Dell Rhea’s Chicken Basket in Willowbrook, Ill., which was featured on TV show “Diners, Drive-Ins & Dives.”
15. Buy maple syrup from Funks Grove Pure Maple Sirop in Shirley, Ill. The Funk family has been making sirop in Funks Grove since 1824.

Missouri

16. Route 66 stretches for more than 280 miles in Missouri. First stop: eat frozen custard at Ted Drewes Frozen Custard in St. Louis, Mo.
17. Stop for selfies at the Historic Route 66 Overlook, which affords a panoramic view of the Wooden Railroad Trestle Bridge in Devils Elbow.
18. Slip into a booth and slip back in time at the Route 66 Diner in St. Robert, Mo. Open 24/7, this 1950s diner serves burgers, fries and shakes. Pop some quarters in the jukebox to enjoy some tunes while waiting for your food.
19. Pose for photos in front of the Route 66 Mural, a 15-foot by 32-foot mural by artist John Biggs that depicts the Chicago and St. Louis skylines on the Bruner Building in downtown Webb City, Mo.
20. Catch a blockbuster movie at the 66 Drive-in Theatre in Carthage, Mo.

Kansas

21. Although Kansas has the shortest stretch of Route 66 – only 13 miles – there’s plenty to see and do. Start by driving along the Old Route 66 Boulevard, the older version of Route 66.
22. Then, stop to stroll along the old Galena shopping district to take photos of old storefronts, many of which have been meticulously restored.

Oklahoma

23. There are more than 400 miles of Route 66 in Oklahoma. Explore the Route 66 Museum in Clinton, Okla., which is brimming with Americana like a neon Route 66 sign and a classic car. The museum’s exhibits are arranged by decade, beginning with the 1920s when the route was initially constructed.
24. Stop for nostalgia at Lucille’s Service Station & Roadhouse in Hydro,, Okla. The station is no longer operational but the vintage gas pumps make for nifty photo ops.
25. Learn more about America’s highway and take a “drive” down memory lane at the National Route 66 & Transportation Museum in Elk City, Okla. The museum includes a vintage 1955 pink Cadillac and a mock drive-in theater.
26. Visit the Coleman Theatre filled with Vaudeville history in Miami, Okla. Today, the theater hosts concerts, plays and silent films.
27. Fill ‘er up at POPS in Arcadia, Okla. Even though it’s a newer addition to the historic highway, it’s worth stopping to fill the tank, admire the collection of 12,000 soda pop bottles and choose from 650 kinds of soda at POPS.
28. Get snap happy with the world’s largest concrete totem pole at Ed Galloway’s Totem Pole Park in Chelsea, Okla.
29. Drive thru for a burger at Waylan’s Ku-Ku Burger in Miami, Okla. The building resembles a giant cuckoo clock and is a throwback burger joint sure to please the whole family.
30. Motorcycle buffs must stop at the Route 66 Vintage Iron Motorcycle Museum in Miami, Okla., which includes displays of vintage and rare bikes plus artifacts from Evel Knievel.

Texas

31. Stop for a photo-op at the iconic U-Drop Inn in Shamrock, Tex., which is now home to the city’s Chamber of Commerce.
32. Route 66 is full of random artifacts and tacky tourist delights like the Devil’s Rope and Route 66 Museum, which the website describes as “Everything you want to know about barbed wire and fencing tools.” Intriguing.

New Mexico

33. Admire Tucumcari Mountain, as it pokes up off the plains southwest of Tucumcari, N.M.
34. Snap photos of the motels and 1950s diners with restored neon signs along this stretch of the route.
35. Go SCUBA diving in the Pecos River in Santa Rosa, N.M., an oasis of artesian lakes, its Blue Hole plunging 240 feet beneath the stark desert floor.
36. Wind westward through the wooded foothills of the Sangre de Cristo Mountains and drive among Hispanic villages, which is populated with adobe churches that predate Route 66 by roughly a century.
37. Tour Pecos National Historical Park, a complex of ancient Pueblo ruins and two Franciscan missions dating from the 17th and 18th centuries.
38. Visit San Felipe de Neri, a vintage 18th century church in Albuquerque, N.M.
39. Heading south from Albuquerque to Los Lunas, N.M., the byway sidesteps Isleta Pueblo before it veers west to Correo and the Parker Pony Truss Bridge near I-40. Drivers may opt to stay on a rough section of the byway or briefly jump on I-40 to Mesita, N.M. where the byway slices through some spectacular red-rock cliffs past Dead Man’s Curve and Turtle Rock.
40. Take a rest at Pueblo of Laguna, which is perched on a hilltop where travelers may glimpse the whitewashed San Jose de la Laguna Mission Church.

Arizona

41. The road’s longest continuous stretch – some 140 miles on the state’s western side – is packed with places to see and things to do. Start in the former mining boomtown of Oatman, Ariz. used as a set for the 1962 film “How the West Was Won.”
42. Spend the night in the Oatman Hotel. Built in 1902, it is the oldest two-story adobe structure in Mohave County. Check out the famous honeymoon suite where Clark Gable and Carole Lombard bunked after their wedding in 1939. Look out for “Oatie the Ghost,” a friendly poltergeist whose identity is believed to be that of William Ray Flour, an Irish miner who died behind the hotel, presumably from excessive alcohol consumption.
43. Nearby, take an underground tour of Gold Road Mine, which was active until 1998.
44. Stop in Peach Springs, tribal headquarters for the Hualapai Nation and the place to book Colorado River and Grand Canyon West adventures if you’re looking for an extended road trip detour.
45. Check out Grand Canyon Caverns, a natural limestone cave system 210 feet underground.
46. Buy souvenirs at the Route 66 Gift Shop in Seligman, Ariz.
47. Eat at the family-owned Sno-Cap Drive In, a wacky burger joint in Seligman, Ariz.
48. Briefly drive on I-40 to admire the 1930s storefronts in Ash Fork, the self-proclaimed “Flagstone Capital of the U.S.”
49. Spend the night at the Red Garter B&B and Bakery, a beautifully restored two-story Victorian Romanesque saloon and bordello built in 1897.
50. Stop for a refreshing ice cream soda or vanilla Coke at Twisters, a 1950s soda fountain in Williams, Ariz.
51. Ride along arguably the nicest stretch of Route 66 in Arizona: Williams. Williams was the last town on Route 66 to be by-passed by Interstate 40 in 1986. Many of the buildings along this stretch of Route 66 were constructed in the late 1800s.
52. About eight miles of Route 66 runs through Flagstaff, Ariz. northern Arizona’s largest city. The Art Deco storefronts, neon-signed motels, and the historic railroad depot here all make great backdrops for photos. Visit The Museum Club, a country-western bar entered through a wishbone-shaped tree trunk.
53. Head east to Winslow, Ariz. where La Posada, a 1930s railroad hotel created by Mary Colter, which was refurbished in the 1990s.
54. Sleep in a wigwam at the Wigwam Village #6 just west of downtown Holbrook, Ariz.
55. Admire the mighty Colorado River as you enter California.

California

56. Once a major stop along Route 66, Needles, Calif. has struggled (like many small towns along the route) as large interstates were built. Stop to take in the scene of bygone times.
57. Pass through the ghost town of Amboy, Calif., easily recognizable by the large and colorful “Roy’s Motel Café” sign.
58. If you’re riding Route 66 on a motorcycle, escape the unrelenting sun of the Mojave Desert by standing under the canopy at Roy’s Motel Cafe, a defunct gas station, motel and cafe.
59. Speaking of motorcycles, you should definitely ride one for part of the route.
60. Before leaving Amboy, Calif., check out Amboy Crater National Landmark, an impressive symmetrical volcanic cylinder cone.
61. Stop by the original McDonald’s in San Bernardino, Calif.; however, you won’t be able to order a Happy Meal here as it is now the First Original McDonald’s Museum.
62. Stay in the iconic teepee-shaped cabins at Wigwam Village #7 in San Bernardino, Calif.
63. As you pass through Los Angeles, make time to check some – or all – of our 52 Super Cool Things to Do in Los Angeles items off your must-see list.
64. Route 66 passes through Beverly Hills, so be sure to watch for celebrities.
65. Snap selfies at the end of Route 66, which is at the Santa Monica Pier. Since 2009, there is an official sign that says “Santa Monica 66 End of the Trail” so travelers can take the requisite road selfies to prove they made it.
66. Plan your next road trip! Fortunately, there are many flights from Los Angeles International Airport, making it easy to start your next journey the minute your road trip ends.

Main image: iStockPhoto/Lise Gagne