The 25 Most Important Cities on Route 66

Route 66 is one of the most famous roads in the World. Not because it’s the most spectacular or the longest, but because it symbolizes some of the core values of the United States: diversity and freedom found in the 25 most important cities on Route 66.

We have been asked many times about the U.S. Route 66 major cities, and we always come to the same conclusions.

For this reason, we thought that it was necessary to write an article on this subject. So here, we have made a compilation of the 25 must-visit Route 66 cities.

25 Must-Visit Cities on Route 66

• Check Out: EZ66, Route 66 Travel Guide
• Route 66 Map

1. Chicago, Illinois

Chicago is one of the U.S. Route 66 major cities you’ll find on your historic Route 66 road trip.

The city of Chicago, known as “The Windy City,” is architecturally beautiful, with many places to see.

It is a city on Route 66 whose fundamental development occurred in 1850. Its nickname does not come from the wind but from the widespread corruption in the political sphere.

Chicago suffered from a huge fire in 1871 that destroyed much of the city. At the time, many of the buildings were made of wood, and the fire quickly spread throughout the city.

However, after this great fire, many renowned architects came to the city to collaborate in its reconstruction.

During this time, the end of the nineteenth century and the beginning of the twentieth century, the city’s architectural style that we know today as the Chicago School developed.

Here’s a whole article about the best things to do in Chicago in 1-day and if you have more time, plan your trip to Chicago in 4-day with this complete itinerary

What you can’t miss in Chicago is this:

Route 66 Start Signal

This point has changed over time, but it initially began leaving Jackson Blvd. and Michigan Ave.

However, in 1955, they changed Jackson Blvd’s direction. Adams St. became the main avenue with an East-West direction.

Still, they kept the starting point on Jackson Blvd. with Lake Shore Drive. Therefore, it is more of a formality than anything else since Route 66 has never actually started from this point.

If you came from Los Angeles, the endpoint was more accessible (after 1933, it was at Jackson Blvd. and Lake Shore Drive, and by 1933 it was at Jackson Blvd. and Michigan Ave.).

• Check Out this guided tour

Lou Mitchell’s

Lou Mitchell’s is a Route 66 classic. It is where travelers come to eat breakfast before starting Route 66. It has been open since 1926 and is crucial to visit when traveling on Route 66.

Pizzeria One

The “Deep-dish pizza” was invented here, later becoming the Chicago-style pizza. Pizzeria One opened in 1943 and quickly became famous for the taste and quality of its “Deep-Dish pizza.”

2. Joliet, Illinois (One of the Best Cities in Route 66)

Known as “The City of Spires,” it has pointed spires in the area for many churches. In addition, this city on Route 66 has been featured in well-known films such as “The Blues Brothers,” “Natural Born Killers,” and “Public Enemies,” as well as in series such as “Prison Break.”

When you get to Joliet, you cannot miss these places.

Joliet Area Historical Museum and Route 66 Welcome Center

Joliet’s historical museum is dedicated to Route 66, with different exhibitions and attractions such as The Road on the Ceiling, the Blues Brothers Photo Op, the Drive-in Diner, Route 66 Drive-in Theater, and the Route 66 Motel Room.

The Old Joliet Prison

Appearing in the film “The Blues Brothers” and the television series “Prison Break,” entry is not allowed for now, but they consider sightseeing tours of the prison.

3. Wilmington, Illinois

Wilmington is a small town, but it has a monument that is a Route 66 classic.

Gemini Giant to See in One of the Best Cities on Route 66

In Wilmington, you can see the “Gemini Giant,” one of the giant classics placed along many routes and roads in the United States, including Route 66.

They are about 20 feet high (7 meters approx.) and usually have one hand with the palm up and the other with the palm down to hold some tool or element. They are known as the “Muffler Men” because they were usually placed in front of car shops and usually held car mufflers.

In the case of the Gemini Giant, he’s got a rocket in his hands, and he wears a big helmet.

The design is very different from other giants because it was redesigned to advertise the café, the “Launching Pad,” where it sits in front. The giant was redesigned to turn it into a kind of astronaut with a rocket in his hands.

Read the full and detailed post on what to see on the stretch from Chicago to Bloomington.

4. Bloomington, Illinois

Bloomington has more than 150,000 inhabitants and is located in the heart of Illinois. The people of Bloomington are especially proud of their Midwestern hospitality. The city of Normal is located north of  Bloomington.

Tourists often confuse one city with the other because you don’t know when you cross from one to the other.

In Bloomington, you can visit:

First Steak ‘N’ Shake

This location dates back to 1934, when Gus Belt founded the first restaurant based on the highest quality burgers and smoothies. Now, there’s a restaurant called Monical’s Pizza.

Quinn Shell Station

This service station has operated for over 70 years. It has been part of the Illinois Route 66 Hall of Fame since 2012. But, unfortunately, it’s permanently closed at the moment.

Lucca Grill

It began in 1936 and served Italian food, especially famous for its crispy and thin pizza. A fun fact about the place is that the roof is entirely made of carved mahogany wood.

5. St Louis, Missouri

Among the cities on Route 66, you have to visit St. Louis. Two Frenchmen founded it in the mid-18th century.

However, it changed ownership at the end of the same century, first passing into Spanish hands and later becoming part of the United States in the early nineteenth century.

It was one of the starting points of the travelers who explored the American West during the 19th century.

Three bridges can cross St. Louis, and depending on the bridge you travel to, you can see different sites and attractions. The three bridges are:

• McKinley Bridge.
• New Chain of Rocks Bridge (the new, not the old one).
• McArthur Bridge.

You can also see the Eads Bridge. It is named after its builder and is the oldest steel bridge and the first to be built with cantilevered beams in 1874.

• Check Out The Best Things to do in Missouri
• The best things to do in Saint Louis, MO

In St Louis, I recommend you to visit:

The Gateway Arch

It is an arch made of stainless steel that reaches up to 190 meters high. It is the tallest monument in America made by people.

Tickets can be purchased to access the arch’s interior and the top from a stunning view. The arc represents the expansion of the United States. The entrance gives access to exhibitions about America’s westward development.

Jefferson National Expansion Memorial

This memorial is a 37-hectare park where you will find The Gateway Arch, the West Expansion Museum, and a former Federal Courthouse.

You’ll get an idea of what Lewis & Clark did on their famous expedition to the West, and you can also board a 19th-century boat for a short tour of the Mississippi.

Check out the full article about the stretch from Bloomington to St Louis from Route 66

6. Cuba, Missouri (One of the Route 66 Cities for Mining and Farming)

In honor of the island of Cuba, this city was founded in 1857, and most of its inhabitants were engaged in mining or farming. At the beginning of the twentieth century, it was known as “The Land of the Big Red Apple.” In 1931, Route 66 arrived, and the business grew.

You can not drive on Route 66 and not admire the Murals of Cuba. This city contains plenty of murals well preserved and restored. They’re a Route 66 classic! The Missouri Chamber and Senate have named it “Route 66 Mural City.”

It is highly recommended to take a walk around the city to see them.

7. Lebanon, Missouri

Lebanon is the largest town between Rolla and Springfield, Missouri. It became an essential stop on Route 66 cities.

Different services were provided to travelers, such as motels, shops, gas stations, restaurants, etc. Springfield

Best things to visit in Lebanon

Munger Moss Motel

The Munger Moss Motel is a classic on the road with a good collection of toy trucks.

The Munger Moss was a sandwich shop that first opened at Devil’s Elbow around 1940 and moved to Lebanon in 1946 with the highway’s modification.

Taking advantage of the transfer, they turned it into a Motel and were acquired in 1971 by Bob and Ramona Lehman, who are well known for their defense and promotion of Route 66.

Route 66 Museum

Opened in 2004, you can see the life of the old businesses on Route 66, such as a Texaco service station, a hotel room from the 20s and 30s, and a typical bar with its painted cook, which gives the impression that is looking at you from the kitchen.

8. Springfield, Missouri

Springfield is the largest city in southern Missouri, although one might think differently due to all the shallow houses at first sight.

They extend over a vast surface area. For example, on Saint Louis Street to the east of downtown, you can feel the atmosphere of Route 66 in the facades and decorations.

Watch out because the speed limit is only 20 miles per hour!

Here’s the detailed post about the stretch of Route 66 from St. Louis to Springfield.

9. Carthage, Missouri

Carthage is a typical city of Route 66 and retains many of the places that made this route what it was.

Carthage is a city that has seen everything; Indian settlement, the Civil War, and prosperity thanks to the discovery of minerals and mines in the area.

In Carthage, I recommend you see:

The 66 Drive-In Theater

It’s another one of those typical American movie theaters where you watch the movie from your car. It was built in 1949 and reopened in 1998. But, unfortunately, they’ve been using it as a junkyard.

It is the last of the six Drive-In theaters to open with Route 66. However, it is still operational on weekends from April to September.

Boots motel

This motel was famous for serving breakfast at any time of the day. It underwent quite a few changes of ownership and nearly disappeared.

It was reopened in 2012 and gradually restored by the two sisters who bought it: Debye Harvey and Priscilla Bledsaw.

10. Joplin, Missouri

Joplin is the last or first city you visit in Missouri. It was founded simultaneously as Carthage, and for an extended period, these two cities on Route 66 had individual rivalries.

Joplin has many things to do and is very well-preserved. It is highly recommended to go through the Main St. of this city and drink a coffee. You can also admire the Thomas Hart Benton Mural or go to one of Bonnie & Clyde’s hideouts.

11. Vinita, Oklahoma

Vinita is Oklahoma’s second-oldest city. One of the towns that experienced the Trail of Tears first-hand was the forced removal of the Cherokee people from their native lands.

In Vinita, you have many places to see.

Hotel Vinita

It’s on the National Register of Historic Places. It was built in 1930 and is on Route 66 itself, in the center of Vinita.

McDougal Filling Station

It is registered on the National Register of Historic Places. It is a house-type service station built in 1940 on Route 66.

Clanton’s Café

It is the oldest restaurant on Route 66 in Oklahoma and still operating.

12. Catoosa, Oklahoma

Catoosa is known only for one attraction: “The Blue Whale.” It is a blue whale that was in a pond and was part of a small water park. It’s an icon of Route 66. However, there are many other things to see in this small town. Don’t miss it.

13. Tulsa, Oklahoma (One of the Best Route 66 Cities with Native American Heritage)

Cyrus Avery was born in Tulsa, Oklahoma, and is known as “The Father of Route 66.” Today, it has more than 400,000 inhabitants and is a city where you can find Native American heritage, remanents from the days of the oil boom, and, of course, icons of Route 66.

You have a lot to see in Tulsa; listing everything here would be impossible.

However, I recommend you see:

The Blue Dome

It’s a Gulf gas station that was built in 1926; it was also a car workshop.

Center of the Universe

It can only be accessed by walking and is a classic stop for tourists and one of the “mystery points” of Route 66. What is especially important are the acoustic properties of the environment.

There’s a point that you can stand on, where, when you speak in a normal tone(not too high), you’ll be able to hear the echo of your voice, which comes back to you with much more strength and volume than what you spoke originally.

Furthermore, the people outside the circle/point hear nothing since only you can hear it.

Downtown Tulsa

It is Art Deco style and worth a quiet walk. You can see many buildings corresponding to the beginning of the twentieth century.

It is deeply appreciated how Route 66 has influenced this city’s development and the businesses located on the route: today, 11th Street.

• Check Out: the detailed stretch of Route 66 from Springfield to Bristow.

14. Oklahoma City, Oklahoma

Oklahoma City is the capital of the State of Oklahoma. It is a city with a lot of history, which has also been able to respect the old neighborhoods and architecture. So give it some time to get to know it.

In Oklahoma City, you can see:

Ann’s Chicken Fry House Restaurant in this Route 66 City

It opened in 1948 as a “Cities Service” service station and in 1966 changed business and transformed into a restaurant called “Three Bulls Steak House.” In 1971 his owner’s brother joined the business, and they changed the restaurant’s name.

The way they chose the new name was curious. They put many names in a hat, including their wives, and Ann’s came out.

It’s a must-stop for Travelers on Route 66, even if you’re not hungry. (Closes on Sundays).

Milk Bottle

On Classen Avenue, you can see the famous bottle of milk. It’s a triangular building that’s got a giant milk bottle on it.

Many businesses have owned this place, but the milk bottle goes on, with a slight modification to the color (they paint it from time to time).

15. Clinton, Oklahoma (One of the Humble Route 66 Cities)

Clinton is a town where you must stop and dedicate a little time to it. It was founded in 1903 and is still a thriving town.

Oklahoma Museum of the Route 66 City

Here you can see some history of Route 66 told decade by decade. Here, you can see neon posters of old motels and rooms with classic cars. In some, you can get in and take a photo!

16. Shamrock, Texas

Shamrock owes its name to an Irish immigrant who, in 1890, opened a post office a few miles from where the village is located today.

Its biggest celebration of the year is St. Patrick’s, so if you’re here on March 17th, you can enjoy this day together with its inhabitants.

When you visit Shamrock, walk along Main St. There, you’ll find typical, historic, and classic buildings of Route 66, some of which are:

Conoco Tower Station. U Drop Inn and U Drop Café

It is very typical and a classic of Route 66. It used to be called Nunn’s Café; you’ll see some reference to it under this name.

That’s how it was known then since John Nunn was its first owner. It was Shamrock’s first business on Route 66.

Magnolia gas station

It is a restored service station. The Magnolia Petroleum Company was established in 1911. In 1925 it was added to Standard Oil, and in 1959 it became Mobil.

In fact, Mobil’s current logo is Magnolia’s Shattered Glue.

17. Amarillo, Texas (One of the Largest Route 66 Cities)

Amarillo is the largest city you’ll find between Oklahoma City and Albuquerque.

The city was first named “Oneida” but soon changed to Amarillo. This Spanish word referred to the color of the land (yellow) on the benches near Amarillo Creek and the abundant yellow wildflowers during the spring and summer.

Needless to say, the name was given by Spanish-speaking explorers. So logically, the pronunciation in Spanish has been lost.

Although there are many places to see here, there are two that stand out, which, of course, are absolute classics of Route 66:

Big Texan Steak Ranch

Before entering Amarillo, you can see the Big Texan Steak Ranch. This restaurant is famous all over America because everything here is huge.

The most famous is the 72 Ounce Steak, and the restaurant bets you that if you order a 72-ounce Steak with all of its accompaniments and finish it, you don’t pay it; otherwise, it’s 72 bucks.

Needless to say, finishing it is almost impossible. It quickly became famous, and it’s even featured in an episode of the Simpsons.

It used to be on Route 66 but was moved when the interstate arrived.

Cadillac Ranch

Leaving Amarillo, one will encounter Cadillac Ranch:  a work of urban art commissioned by local representative Stanley Marsh to a group of artists who called themselves “the Ant Farm.”

This group was founded by two architects in the 1960s and involved numerous artists.

Cadillac Ranch consists of 10 Cadillacs partially buried in the ground at an angle, pointing their trunks towards the sky.

The tradition is to go with a spray can and leave a mark on the cars(graffiti). But, don’t worry, and it’s part of the artwork.

They are periodically repainted in base color so that they can be re-graffitied. Its current location is not the original, as it was moved when Route 66 was removed from its original route.

Some authors say it was never on Route 66, but it is a must-stop for all travelers who drive on Route 66.

• Here’s the full stretch from Clinton to Amarillo on Route 66.

18. Santa Rosa, New Mexico

When Route 66 passed through Santa Rosa in 1930, the town was filled with service stations, cafés, and motor courts to accommodate motorists traveling the Mother Road.

You’ll see plenty of buildings and signs that take you back to the glory days as you travel Historic Route 66 in Santa Rosa.

Don’t miss:

• Drive on old Route 66 and search for old neon signs
• Route 66 Auto Museum
• Fat Man sign in Route 66 Auto Museum

19. Santa Fe, New Mexico (Second Oldest City in the Route 66 Cities)

Santa Fe was founded in 1607 and is the second oldest city founded by Europeans in the United States ( St. Augustine, Florida, is the first as it was founded in 1565).

Santa Fe was the capital of the Kingdom of New Mexico, and its full name was “La Villa Real de la Santa Fe de San Francisco de Asís,” in English: The Royal Town of the Holy Faith of Saint Francis of Assisi.

The church of San Miguel is located here, the oldest church in the United States, built between 1610 and 1612.

Santa Fe is a beautiful city; you will also see many reminiscences of its Spanish past. This city is most appreciated when traveling calmly and without rush; otherwise, you will miss details. Don’t get lost!

The Plaza

It’s been the center of the city for 400 years. It is surrounded by the Old Santa Fe trail, Washington and Lincoln Ave, and San Francisco St.

Governor’s Palace

It is an adobe building that has been the governor’s palace since 1610. It’s in the central square, also known as the Plaza.

It is the oldest public building in the United States that has remained occupied. From 1909 to 2009, it was the Museum of New Mexico.

Turquoise Trail

Turquoise Trail is a beautiful road that joins Santa Fe and Albuquerque. The U.S. government considers it a National Scenic Byway. In other words: a tour with great views or fascinating points to see.

It is a tour with a lot of history, where you will go back in time, and you will see unique villages. It also has many attractions, recreational activities, a good gastronomic offer, and museums. There’s room for everyone!

20. Albuquerque, New Mexico (A Stopover in Route 66 Cities)

Albuquerque is the largest city in New Mexico. As a recommendation, spend some time here where you can have a drink in one of its cafes or restaurants and see some of the city’s murals.

The buildings have a very particular style, the Spanish colonial with a fusion of the native Indians, which they are very proud of.

Like any urban stretch of Route 66, it is full of roadside motels with their classic neon lights and typical car parks for travelers’ cars, which share the roadside with car workshops, cafes, and restaurants.

Buildings and businesses have seen the evolution of the route from the 30s to the 70s. At the end of 1955, Central Avenue or Central Ave had over 100 motels, and it was hard to find a room available in the summer!

Central Avenue

Formerly Main St or Route 66, it came to have more than 100 motels running in 1957, which was its best time. You can see the neons running on if you can walk at night.

Old Jones Motor Company

It was one of the most modern businesses of the time (1939). It included a full-service station with all services. In 1957 it changed places.

In 1993 it was designated as a historic building, and in 1999 it was bought by a couple who liked the building and turned it into what we now know as Kelly’s Brewery. It’s a must-stop.

21. Gallup, New Mexico

Gallup is known as the Native American capital of the World and is famous for its neons on either side of the road.

You have plenty of dining options, such as the Gallup Inn, El Rancho Motel, and Ranch Kitchen. In Gallup, you will also be able to find Native American crafts of all kinds.

22. Holbrook, Arizona (One of the Touristy Route 66 Cities)

Holbrook, which hosts the  Painted Desert, the Petrified Forest, and the Indian Reservation, became a touristy site with Route 66. This led to the creation of many businesses to cater to tourists.

We’re in the middle of what’s called the Wild West.

Here, the traditional cowboy is a classic, and you are surrounded by Indian reservations. I’d advise you not to miss these places:

Wigwam Hotel

Holbrook is well known for its motel with Tipis (traditional Native American tents). It must be one of Holbrook’s most photographed sites.

However, if you want to sleep here, you will have to book at least two weeks in advance!

Geronimo Trading Post

If you want some different memories of Route 66, this is your site! It has all kinds of souvenirs for you to bring to your home. It’s found leaving Holbrook, direction west, about 15 miles away.

23. Flagstaff, Arizona

It is also known as the City of 7 Wonders because of its location in the middle of Coconino National Forest.

It is surrounded by the Grand Canyon, Oak Creek Canyon, Walnut Canyon Wupatki National Monument, Sunset Crater National Monument, and San Francisco peaks.

Founded in 1876, it began its history with the railroad’s arrival in 1881 and Northern Arizona University in 1899.

Tourism became an industry in Flagstaff in the early twentieth century and quickly grew with the arrival of Route 66 and its proximity to the Grand Canyon.

From here, you can make excursions to go to the Grand Canyon. If you have not passed before or intend to go to Las Vegas, it is a good point to go.

Museum Club

It is a must for travelers on Route 66. Built in 1931 as a taxidermist museum, in 1936, its owner died, and it became a nightclub.

Today it is a place to have a drink and enjoy live music. It is a place with a lot of charm and that you should not miss.

24. Oatman, Arizona

Oatman is a mining town preserved since the American Wild West. It’s a rather curious little town where donkeys roam the streets without problems. You’ll see many, and they’ll come up to you to feed them something.

You must keep an eye on when you arrive at Oatman because everything is closed from approximately three o’clock in the afternoon.

In Oatman, you’ll find people who mimic characters from the American West and even fictional shootings and a saloon that’s wallpapered with American dollar bills.

Read the full post we’ve dedicated to Oatman.

If you are in Las Vegas and want to go to Oatman for a guided tour, check this link.

25. Kingman, Arizona (One of the Route 66 Cities Closes to Grand Canyon)

Kingman is the capital of Mohave County in northwest Arizona, and it’s the closest city to the Grand Canyon and is a must-visit place on your Route 66 road trip as Kingman is known as the Heart of Historic Route 66.

It has a good temperature all year long due to its 3,300-foot elevation. 

If you have time, you can stay for a few days to enjoy this city and its surrounding area.

Historic Route 66 Museum

In Kingman, Arizona, the Historic Route 66 Museum was created to preserve Kingman’s history on the famous Route 66. 

Mohave Museum of History & Arts

Mohave Museum of History & Arts is a historical museum in Kingman, Arizona. 

Lake Mohave

In Kingman, Lake Mohave is a 67 miles artificial lake on the Colorado River between Hoover and Davis Dams.

You can enjoy different water activities like fishing, jet skiing, and kayaking here. And also hike the area.

Read the full article about the best things to do in Kingman, Arizona

26. Amboy, California

Amboy is located in the Mojave Desert. It is known for the Roy’s Café sign. In its good times, Amboy had an airport, a church, and a car workshop. But they’re not up and running anymore.

The town became a ghost town many years ago; in 2003, its population was 7 people, and that same year they put the village of Amboy on sale on eBay for $1.9 million. It was not sold. The highest offer was less than $1 million.

• Take a look at the stretch from Amboy to Los Angeles.

Roy’s Motel & Café

It is one of the most photographed attractions on Route 66 of this stretch through California.

27. Los Angeles, California (A Popular City on Route 66)

Los Angeles is either the beginning or the end of Route 66, depending on where you start.

As I always say, Los Angeles is a city one should know. However, it is not my favorite city in the U.S.

There are cities on Route 66 with much more charm in the United States than Los Angeles.

• In this article, I tell you in detail what to see in Los Angeles.

Travel Insurance for Route 66 Cities: Simple & Flexible

Do not forget to take out travel insurance when you travel to the USA. Hopefully, you don’t need to use it, but it is better to be prepared for any eventuality or emergency.

In my case, I have Mondo’s annual insurance, with worldwide medical assistance with coverage of $ 10,000,000. Also, you can use our link to get a 5% discount on Hey Mondo Insurance.

Choosing travel insurance will depend mainly on the duration and coverage of the insurance. It is best to inform yourself well to choose the best insurance available.

If you want, you can check our guide about choosing travel insurance, where you will find comparisons, opinions, and discounts.

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Last Updated on 25 October, 2023 by Veronica