A road trip on Route 66 is the type of journey that fascinates so many, a route laid out in 1926 connecting Chicago to Los Angeles, passing through the heart of the United States, a 2,400-mile road adventure that has always been considered the ultimate road trip.
Along the route, you will encounter bizarre neon signs, historic drive-in cinemas, unlikely diners, kitschy gas pumps and many other characteristic places that will make your journey seem like you are really traveling through time in the cities of the American province.
There are many stops on Route 66 and identifying the original route is not an easy task. In this article, I will suggest an itinerary through some of the best stops on Route 66, a series of must see sights in true “Mother Road” spirit that can be visited even if you don’t travel the entire historic stretch of road to the letter. Also, you will find a list of the best route 66 attractions state by state.
If, on the other hand, you are interested in following the entire route, I recommend our Route 66 road trip planner.
- Preparing for the journey on Route 66
- Route 66 Best Stops: 10 Must See Sights
- Stage 1: Breakfast near Grant Park, Chicago, Illinois
- Stage 2: Gemini Giant, Wilmington, Illinois
- Stage 3: 66 Drive-In, Carthage, Missouri
- Stage 4: Blue Whale, Catoosa, Oklahoma
- Stage 5: Milk Bottle Grocery, Oklahoma City, Oklahoma
- Stage 6: Cadillac Ranch, Amarillo, Texas
- Stage 7: Blue Swallow Motel, Tucumcari, New Mexico
- Stage 8: Wigwam Village Motel #6, Holbrook, Arizona
- Stage 9: Oatman, a Western town in Arizona
- Stage 10: Santa Monica Pier, Santa Monica, California
- Route 66 Attractions State by State
Preparing for the journey on Route 66
The best time to plan your Route 66 itinerary is from May to September. In April, you may still encounter freezing temperatures, hail, incessant rain, high winds and dust storms. Don’t forget that Route 66 runs through the “underbelly” of America, so the weather will vary depending on the stops you make.
There are those of you who will prefer the month of September to travel this route, both due to the climate and the smaller number of tourists that will crowd the road. Either way, be sure to bring all you need to cope with the fluctuating temperatures that you will encounter as you travel from one place to another.
You’ll find wide roads in front of you, sometimes with uneven surfaces, long stretches of straight road, and sometimes desolate landscapes. You will maybe need to rent a car to face the route, if you don’t use your car.
Don’t forget to bring a good map of the United States of America (the Rand McNally Road Atlas or the Michelin guides) and a GPS with you: some stretches are not always easy to find.
Route 66 Best Stops: 10 Must See Sights
If you are interested in retracing the Mother Road to the letter, please refer to our guide on how to identify the original route of Route 66. If, on the other hand, you are interested in visiting the main points of interest on the road, here are 10 stops to include in your itinerary (in order from Chicago to Los Angeles):
Stage 1: Breakfast near Grant Park, Chicago, Illinois
as you may have read in our article on the best attractions in Chicago, Grant Park is a large urban park located in the business district, whose main attractions include the Millennium Park, which is teeming with state-of-the-art architectural structures, the Buckingham Fountain, one of the largest fountains in the world, the Art Institute of Chicago, and the Museum Campus.
Are you wondering what this park has to do with Route 66? Well it does, for a very simple reason. It is here, at the intersection of Jackson Boulevard and Michigan Avenue, that you will see the sign that reads “End of Historic Route 66“. In fact, “The Main Street of America”, the mother of all American Roads and routes ends at this point, and if you want to see the sign of the beginning, you just need to move a few yards onto Adams Street East (here are some more details on where Route 66 starts and ends).
You might say: it’s not worth stopping in one place just to see this sign… maybe you’re right, in fact, the real purpose is another: no trip starts on the right foot without the right breakfast and in fact, nearby, you will find the Intelligentsia Coffee, the perfect place to top up the energy you need for your adventure.
The great thing about this coffee shop is that it is part of a local chain that roasts its own coffee beans, and they are truly masters of the art of filtering. Sit at a small table in the window and watch the daily hustle and bustle of Chicago as you sip your delicious coffee.
Stage 2: Gemini Giant, Wilmington, Illinois
Statues of giants called “Muffler Men” were once widespread on Route 66, characterizing nearly every single attraction, but over time these imposing figures disappeared along with the businesses they sponsored; however, a few still remain, and the Gemini Giant in Illinois embodies an example of them in its own special way.
Usually, the original “Muffler Men” were based on the figure of the ax-wielding lumberjack (Paul Bunyan), although each one was then somehow adapted to the needs of the business or attraction it represented. This was also the case for the Gemini Giant, who stood “guard” over the Launching Pad Drive-In, whose name was taken from the Gemini space program. He was dressed in a helmet and spacesuit, holding a missile with the name of the diner written on it.
- What to look for: the giant himself and as you can imagine, he won’t be hard to notice.
- Where to find him: S East St, Wilmington, Illinois.
Stage 3: 66 Drive-In, Carthage, Missouri
On a trip this long, you’ll need a few moments of entertainment. Why not stop at one of the few remaining drive-in theaters in the world and enjoy a show or two? Why 2? Because the second one is free!
The drive-in theater in Carthage, Missouri opened in 1949 and closed in 1985. In 1998 it was reopened and renovated, and now plays movies every week on Fridays, Saturdays and Sundays. Make plans to stop by at the right time!
- What to look for: the neon sign bearing the name of the venue.
- Where to find it: at 17231 Old Route 66 Boulevard, Carthage (Brooklyn Heights), Missouri.
Stage 4: Blue Whale, Catoosa, Oklahoma
Crossing Route 66 in Oklahoma, at a certain point you will notice on your right a small lake where a whale lies undisturbed. It was built by a local resident, Hugh Davis in 1972 for his wife as a 34th wedding anniversary gift. After the death of the creator, the bizarre sculpture began to deteriorate but fortunately in 1988, his son repaired it to its full shape. Like the “Muffler Men,” gas pumps and neon signs, this is one of Mother Road’s most recognizable and iconic attractions.
- What to look for: a large whale in a pond.
- Where to find it: 2600 Route 66, Catoosa, Oklahoma.
Stage 5: Milk Bottle Grocery, Oklahoma City, Oklahoma
Route 66 is known for kitsch, so if you just can’t resist this kind of attraction, near Oklahoma City there is a giant milk bottle waiting for you on top of a small triangular building.
It is a food store where you can buy refreshments, eat some local specialties (for example the famous Vietnamese banh mi sandwich), or drink a good, iced coffee.
- What to look for: a giant milk bottle. How can it go unnoticed?
- Where to find it: on North Classen Boulevard, Oklahoma City, Oklahoma.
Stage 6: Cadillac Ranch, Amarillo, Texas
What do you do if you have a lot of Cadillacs left over? Plant them face down in the desert, of course! That was the crazy idea of Chip Lord, Hudson Marquez and Doug Michels, who created this bizarre installation in 1974, which has now become a sort of institution of US tourism. To learn more, read our article on how to visit Cadillac Ranch.
- What to bring: spray paint! The Cadillac Ranch is one of the few places where you can unleash the artist in you by creating graffiti.
- Where to find it: along I-40 (old Route 66), just outside of Amarillo.
Stage 7: Blue Swallow Motel, Tucumcari, New Mexico
One of the most interesting aspects of Route 66 is that the businesses that have sprung up along this road are actually small family firms that proudly stand out from the widespread American chains. The Blue Swallow Motel, which makes hospitality and warmth its main quality traits, is certainly one of them: here it is said that in the ’50s, penniless travelers were allowed to stay in exchange for personal items or even for free. But what makes this motel famous throughout Route 66 is undoubtedly its sign, one of the most characteristic to be photographed along the route and with a clear message: just as the swallow indicated land for the sailor, every traveler on the road can see the signal of home in this flashy sign.
- What to look for: one of the most beautiful neon signs on Route 66.
- Where to find it: 815 E Route 66 Blvd, Tucumcari, New Mexico.
Stage 8: Wigwam Village Motel #6, Holbrook, Arizona
Indian tents made of concrete and steel…that you can sleep in! Of course, you could find more spacious hotels, but what fascinates here is the environment, in full Route 66 spirit.
In 1938, Mr. Chester E. Lewis found himself in Kentucky and was particularly impressed by the Wigwam Village in Cave City, built the year before by the architect Frank Redford. Determined to reproduce the idea, he made agreements to exploit the name. According to the contract, Mr. Lewis would install coin-operated radios on the site and pay Mr. Redford a royalty for their use. There were 7 Wigwam Villages built up to the ’50s and the one we are talking about was the sixth (hence the designation #6).
A curious detail comes from the fact that the name “wigwam” was not quite appropriate for the site: a wigwam is in fact a dome-shaped dwelling used by Native Americans, while those actually built were the typical conical-shaped Indian tents (so more appropriate to call them “tepees”).
- What to look for: original handmade American walnut furniture, classic cars and Route 66 memorabilia.
- Where to find it: 811 West Hopi Drive, Holbrook, Arizona.
Stage 9: Oatman, a Western town in Arizona
Are you ready to visit an authentic old Western town with donkeys roaming the streets and weekend shootings? This is Oatman, a small mining town built in the early 1900s on “Bloody 66,” the most dangerous and rugged stretch of the Mother Road. To learn more about how to get there and how to visit it, check out our in-depth post: How to Visit Oatman in Arizona.
- What to look for: the Oatman Hotel, where Clark Gable and Carole Lombard spent their honeymoon on March 18, 1939.
- Where it’s located: in the Black Mountains, not far from the Arizona-California border, about 45 miles from the town of Kingman.
Stage 10: Santa Monica Pier, Santa Monica, California
Continuing on your journey, at the end of the Route you will find yourself in California and, continuing on towards the ocean, you will land at the quaint Santa Monica Pier, with its amusement park and the famous Ferris wheel on the beach. This is one of the best-known coastal attractions that, in addition to providing tourist entertainment, admirably illuminates the coast at night.
There has been much debate as to where Route 66 ends: for some, it is at the intersection of Olympic Boulevard and Lincoln Boulevard, for others it is at the intersection of Santa Monica Boulevard and Ocean Avenue.
In either case, you’ve arrived and while you’re there, why not continue on to Palisades Park? This is a beautiful public park along Ocean Avenue with manicured lawns, tall palm trees, sculptures and paved paths. As it is located on top of the Santa Monica cliff, you can also enjoy a beautiful panoramic view of the beach and the Pacific Ocean.
- What to look for: the historic carousel, the Ferris wheel, the street performers, and, of course, the end of the line on Route 66!
- Where to find it: on the 200 Santa Monica Pier, Santa Monica, California.
Route 66 Attractions State by State
Here is a list of the things to see and the best attractions of Route 66 state by state:
Route 66 Illinois Best Attractions
- Grant Park (Chicago)
- Gemini Giant (Wilmington)
- Ambler-Becker Texaco Station (Dwight)
- Murals (Pontiac)
- Chain of Rocks Bridge (Madison)
- Henry’s Rabbit Ranch (Staunton)
Find more information on these and other places to visit in our article: Route 66 Illinois
Route 66 Missouri Best Attractions
- Gateway Arch (St. Louis)
- 66 Drive-In (Carthage)
- Red Oak II (Carthage)
- Wagon Wheel Motel (Cuba)
- Meramec Caverns (Sullivan)
- Munger Moss Motel (Lebanon)
- The Giant Rocking Chair (Fanning)
Find more information on these and other places to visit in our article: Route 66 Missouri
Route 66 Oklahoma Best Attractions
- Blue Whale (Catoosa)
- Milk Bottle Grocery (Oklahoma City)
- POPS (Arcadia)
- Old Round Barn (Arcadia)
- Conoco Station (Commerce)
- Oklahoma Route 66 Museum (Clinton)
Find more information on these and other places to visit in our article: Route 66 Oklahoma
Route 66 Kansas Best Attractions
- 4 Women on the Route (Galena)
- Nelson’s Old Riverton Store (Riverton), formerly called Eisler Brothers Store
- Historic Rainbow Bridge (Riverton)
- Tri-State Marker (Baxter Springs)
Find more information on these and other places to visit in our article: Route 66 Kansas
Route 66 Texas Best Attractions
- Cadillac Ranch (Amarillo)
- Big Texan Steak Ranch (Amarillo)
- Buggy Ranch (Conway)
- U Drop Inn (Shamrock)
- Britten Leaning Water Tower (Groom)
- Route 66 Midpoint (Adrian)
- Phillips 66 Station (McLean)
Find more information on these and other places to visit in our article: Route 66 Texas
Route 66 New Mexico Best Attractions
Find more information on these and other places to visit in our article: Route 66 New Mexico
Route 66 Arizona Best Attractions
- Wigwam Village Motel #6 (Holbrook)
- Petrified Forest National Park
- Grand Canyon
- Oatman Ghost Town
- Historic Seligman Sundries (Seligman)
- Grand Canyon Caverns (Peach Springs)
- Museum at Powerhouse Visitors’ Center (Kingman)
Find more information on these and other places to visit in our article: Route 66 Arizona
Route 66 California Best Attractions
- Roy’s Motel (Amboy)
- Bagdad Café (Bagdad)
- Calico Ghost Town (Barstow)
- Elmer’s Bottle Tree Ranch (Helendale)
- Original McDonald’s Museum (San Bernardino)
- Aztec Hotel (Monrovia)
- Santa Monica Pier (Santa Monica)
Find more information on these and other places to visit in our article: Route 66 California