1

History

Image: Christian Linnemann

Let’s start from the very beginning: in 1926, almost 100 years ago, Route 66 was established, covering a total of 2,448 miles. It was one of the original highways built under the then-new Numbered Highway System (also known as the "Federal Highways").

The route famously started in Chicago, Illinois, and stretched all the way to Santa Monica, California, passing through Missouri, Kansas, Oklahoma, Texas, New Mexico, and Arizona. At the time, Route 66 proved to be a quick and easy way to get to the western part of the country, which logically led to an increase in its popularity.

2

Landmarks

Image: Mick Haupt

If you find yourself driving along the 2,448 miles that make up Route 66, you’ll certainly come across a fair share of outstanding landmarks, including American icons like the St. Louis Gateway Arch or the Santa Monica Pier. Not only that, you might want to explore some natural wonders, such as a 50,000-year-old meteor crater located in the heart of Arizona.

However, if you're more interested in landmarks focused on unusual or outlandish topics, there are plenty of roadside attractions worth visiting . For instance, you might want to stop for a few hours in San Bernardino, California, to visit the original McDonald’s location, now turned into a museum.

3

One end of the road…

Image: Arnaud STECKLE

As we mentioned before, Route 66 is too long for us to include every single state it crosses in this article. However, we still felt the need to pay a small tribute to the two ends that "America’s Main Street" was built to connect. With that in mind, let’s start with Chicago, the easternmost point of Route 66.

Originally, Route 66 was commissioned as a quicker way to get from Chicago to Los Angeles in response to the large increase in car ownership that occurred in the 1920s. Route 66 shortened the distance between these two cities by 200 miles, providing an easy-to-follow route for millions of Americans.

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…followed by the other end.

Image: Rocio Abrego

According to a popular saying, "All good things must come to an end," and the gorgeous west end of Route 66 is a living testament to this phrase. The "City of Angels" truly doesn’t need an introduction. In that sense, can you think of a more welcoming image than the warm California sun greeting drivers at the final stop of Route 66?

Interestingly, nowadays Route 66 ends in the equally gorgeous city of Santa Monica, located in Los Angeles County. In any case, the way the U.S. Route 66 Highway Association described the highway during its construction still holds true, and Route 66 can still be described as the "most scenic route from Chicago through St. Louis to Los Angeles ."

5

The "Father of Route 66"

Image: John Benitez

Nowadays, a route connecting Illinois and California seems almost logical, but at the time, it took the efforts of a visionary group of entrepreneurs to plan the construction of Route 66. Among them, one individual stands out, known to history as " The Father of Route 66 ": an Oklahoma businessman named Cyrus Avery.

A resident of Tulsa, Oklahoma, Avery was truly a jack of all trades. Originally a school teacher, he went on to become a businessman, an insurance agent, and an oilman after founding the Avery Oil & Gas Company in 1904. In the 1920s, Avery was a member of the federal board appointed to create the Federal Highway System, where he rallied for the establishment of what we now know as Route 66.

6

Feel like walking?

Image: Capstone Events

Who said that only cars can enjoy Route 66? Certainly not Charles C. Pyle, a Route 66 Association member who, in 1928, launched an innovative campaign to promote the new highway: a foot race from Los Angeles to New York City.

With a distance of 3,400 miles, this gargantuan race had a suitably large prize: $25,000, which today would be just under $400,000. Nearly 300 racers crossed America, passing through Route 66 and several checkpoints along the highway. Ultimately, the race was won by a Cherokee citizen named Andy Payne, who finished the race in 573 hours.

7

Culture inspired by Route 66

Image: Jonathan Gong

It seems only logical that such an iconic route has inspired a plethora of songs, books, and paintings. Let’s take a moment to pay homage to some masterworks of American culture that celebrate everything Route 66 has to offer. Celebrated authors like John Steinbeck and Jack Kerouac have set their novels on the highway, with Steinbeck nicknaming Route 66 "the Mother Road."

Perhaps most famously, songwriter Bobby Troup wrote the song "(Get Your Kicks on) Route 66" while traveling on the highway on a road trip across America. The song became a smash hit in 1946 after it was recorded by the Nat King Cole Trio, and it was subsequently covered by music legends like The Rolling Stones, Chuck Berry, and Bing Crosby.

8

Decommission

Image: Alejandro Luengo

In the 1950s, President Eisenhower sought to upgrade America’s highway system into a more modern network, comprising several new routes that connected all 50 states. In 1956, Eisenhower signed the Federal Interstate Act, unknowingly initiating a series of steps that would eventually lead to the end of Route 66 .

After several decades, Route 66 was officially decommissioned in 1985. However, that doesn’t mean you can’t travel through most of it. Nearly 85% of the original highway is still drivable, with many signs marking where the original route once stood.

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Route 66 State Park

Image: Federico Lancellotti

As we mentioned before, there are plenty of spectacular landscapes to explore along Route 66 if you’re a fan of nature. With that in mind, did you know there’s a state park in Missouri named after Route 66?

Route 66 State Park is located at the site of the former town of Times Beach, Missouri, along the Meramec River. In addition to offering beautiful views and hiking trails, visitors might also enjoy seeing the old Route 66 bridge, which is currently undergoing restoration.

10

The music of the road

Image: Miguel Alcântara

We’ll end this article with a Route 66 fact you might not know. Route 66 has inspired many iconic songs, but did you know that a small part of Route 66 actually plays music on its own?

To encourage drivers to stick to the 45-mile-per-hour speed limit, the New Mexico Department of Transportation came up with a rather ingenious idea: by placing rumble strips at strategic points, cars driving under the speed limit will play " America the Beautiful "!

1

Josephine Baker

Image: Richie Lugo

Josephine Baker was the first Black woman to star in a major motion picture , the 1927 French silent film Siren of the Tropics . During her early career, Baker was among the most celebrated performers to headline the revues of the Folies Bergère in Paris. Her performance in the 1927 revue Un vent de Folie caused a sensation in the city. Her costume, consisting only of a short skirt made of artificial bananas and a beaded necklace, became an iconic image and a symbol both of the Jazz Age and the Roaring Twenties.

Baker was celebrated by artists and intellectuals of the era, who variously dubbed her the "Black Venus," the "Black Pearl," the "Bronze Venus," and the "Creole Goddess." She aided the French Resistance during World War II, and after the war, she was awarded the Resistance Medal by the French Committee of National Liberation, the Croix de Guerre by the French military, and was named a Chevalier of the Legion of Honour by General Charles de Gaulle.

2

Rudy Vallée

Image: Matt Botsford

Rudy Vallée was the first male singer to rise from local radio broadcasts in New York City to national popularity as a "crooner." He had a thin, wavering tenor voice and seemed more at home singing sweet ballads than jazz songs. But his singing, saxophone playing, and the innovative arrangements he wrote for his band attracted the attention of a rapidly increasing number of listeners, especially young women.

Singers needed strong voices to fill theaters in the days before microphones. Crooners had soft voices that were suited to the intimacy of radio; the microphones, in this case, promoted direct access to "a vulnerable and sensuous interior," or, in other words, "a conjured intimacy." Vallée was one of the first celebrity radio vocalists.

3

Bobby Darin

Image: Jack Sharp

Bobby Darin was an American teen idol and, later, an adult crooner who, in 1958, co-wrote and recorded his first million-selling single, "Splish Splash," followed by "Dream Lover" and his covers of "Mack the Knife" and "Beyond the Sea," which brought him worldwide fame.

In the early 1970s, his health was beginning to fail due to a weak heart. The knowledge of Darin's vulnerability had always spurred him on to use his musical talent while still young. Darin died in 1973 at the age of 37 in a hospital recovery room after having open-heart surgery in Los Angeles.

4

Keely Smith

Image: Harry Shelton

American jazz and popular music singer Keely Smith performed and recorded extensively in the 1950s with her then-husband Louis Prima , and throughout the 1960s as a solo artist. The couple were stars in the entertainment business, including stage, television, motion pictures, hit records, and cabaret acts.

They won a Grammy in 1959, its inaugural year, for their smash hit, "That Old Black Magic," which remained on the charts for 18 weeks.

5

The Ink Spots

Image: Jorge Flores

The first band on the list, the Ink Spots was an American vocal pop group who gained international fame in the 1930s and 1940s due to their unique musical style, which predated rhythm and blues and doo-wop .

On January 12, 1939, the Ink Spots recorded "If I Didn't Care," one of their biggest hits, selling over 19 million copies and becoming the 8th-best-selling single of all time. Since they disbanded in 1954, there have been well over a hundred vocal groups calling themselves "The Ink Spots," with and without any original members of the group.

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Ella Fitzgerald

Image: zachrie friesen

A frequent collaborator of the Ink Spots, Ella Fitzgerald was a singer, songwriter, and composer, sometimes referred to as the "First Lady of Song," the "Queen of Jazz," and "Lady Ella." She was noted for her purity of tone, impeccable diction, phrasing, timing, intonation, absolute pitch, and a "horn-like" improvisational ability, particularly in her scat singing.

Outside her solo career, she recorded music with Louis Armstrong, Duke Ellington, and the aforementioned Ink Spots. These partnerships produced songs such as "Dream a Little Dream of Me," "Cheek to Cheek," "Into Each Life Some Rain Must Fall," and "It Don't Mean a Thing (If It Ain't Got That Swing)."

7

Bing Crosby

Image: Alexander Wark Feeney

A one-man orchestra, Bing Crosby was a singer, actor, television producer, radio personality, and businessman. The first multimedia star , he was one of the most popular and influential musical artists of the 20th century worldwide.

In 1948, American polls declared him the "most admired man alive," ahead of Jackie Robinson and Pope Pius XII. That same year, Music Digest estimated that Crosby's recordings filled more than half of the 80,000 weekly hours allocated to recorded radio music in America.

Crosby is one of 33 people to have three stars on the Hollywood Walk of Fame , in the categories of motion pictures, radio, and audio recording.

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Perry Como

Image: Oscar Sutton

Perry Como was an American singer, actor, and television personality who sold over 100 million records worldwide and pioneered a weekly musical variety television show. His weekly television shows and seasonal specials were broadcast around the world. He recorded primarily vocal pop and was renowned for his recordings in the intimate, easy-listening genre pioneered by our newly acquainted friend, Bing Crosby.

In the official RCA Records memorial in Billboard magazine, his life was summed up in these few words: "50 years of music and a life well lived. An example to all."

9

Nina Simone

Image: Artem Bryzgalov

A bigger-than-life figure, Nina Simone was a singer, songwriter, pianist, composer, arranger, and civil rights activist whose piano playing was strongly influenced by baroque and classical music, and accompanied by expressive, jazz-like singing in her contralto voice .

Early in her career, Simone played piano at a nightclub in Atlantic City, where she was told that she would have to sing to her accompaniment. This effectively launched her career as a jazz vocalist. Simone also became known for her work in the civil rights movement during the 1950s and 1960s, and she later fled the United States and settled in France following the assassination of her friend Martin Luther King Jr. in 1968.

10

Screamin’ Jay Hawkins

Image: Music HQ

The closer of this list is one of the most colorful characters in American music. "Screamin' Jay" Hawkins was a singer-songwriter, musician, actor, film producer, and boxer, best known for his powerful, shouting vocal delivery and wildly theatrical performances with macabre props onstage, making him an early pioneer of shock rock.

Screamin’ Jay’s most successful recording, "I Put a Spell on You," was created when the entire band was intoxicated during a recording session where "Hawkins screamed, grunted, and gurgled his way through the tune with utter drunken abandon." The resulting performance became his greatest commercial success and reportedly surpassed a million copies in sales.

1

Tipping everywhere

Image: Sam Dan Truong

Americans tip for almost every service, from coffee to taxis. The standard is 15–20% of the bill. Unlike most countries where service charges are included, tipping is often expected and essential for workers’ income.

Restaurants, bars, and even hair salons rely on it. Since this is not as common elsewhere, tourists often miscalculate or under-tip, causing awkward interactions.

2

Super-sized portions

Image: Nima Naseri

Restaurant portions in the U.S. are notoriously large, often doubling or tripling international standards.

This stems from both historical abundance and marketing strategies that equate quantity with value. All-you-can-eat and combo meals reinforce the "more is better" mentality.

3

College tailgating

Image: Josh Applegate

Fans arrive hours before football games, grilling and partying in parking lots. Tailgating mixes sports passion with social gatherings, showing regional pride and university loyalty.

This uniquely American tradition often shocks outsiders with the devotion shown to local sports.

4

Black Friday mania

Image: Artem Beliaikin

Originating in Philadelphia in the 1960s, Black Friday marks the start of the holiday shopping season. It’s a consumer spectacle tied as much to capitalism as to tradition.

Retailers use extreme discounts to generate sales; the frenzy often leaves international observers bewildered by the ensuing chaos.

5

Wearing patriotic clothes year-round

Image: Shari Sirotnak

Americans often wear flag-themed clothing even outside national holidays. The practice intensifies during major sporting events, but displaying the flag as apparel reflects civic pride in everyday life.

For many outsiders, wearing a flag as clothing seems unusual, yet this custom embodies American individualism and patriotism.

6

Driving everywhere

Image: why kei

Unlike many countries with extensive public transit, Americans rely heavily on cars. Suburban expansion and urban planning favor personal vehicles.

Gas prices, infrastructure, and cultural identity reinforce driving as normal. Tourists accustomed to walking or trains find long drives mandatory, and as a result, the layout of U.S. cities is unusually spread out.

7

High school proms

Image: Long Truong

Proms evolved in the 20th century as a rite of passage. Teenagers dress formally for dances with elaborate rituals, including crowning kings and queens.

While other countries almost always have some form of graduation celebrations, the formality, expense, and emphasis on dating customs in American proms often confuse foreigners.

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Obsession with college sports

Image: Riley McCullough

Universities dominate cities with massive stadiums and fanfare. College football and basketball inspire loyalty rivaling professional leagues.

The intensity is unusual internationally, where professional sports typically overshadow collegiate athletics.

9

Yard sales

Image: Clem Onojeghuo

Communities host sidewalk sales for secondhand goods. This tradition emphasizes recycling, community interaction, and bargain hunting.

This casual sale of used goods in public spaces is uncommon in many countries, making it a uniquely American practice.

10

Spelling bees

Image: Brett Jordan

Americans hold intense competitions where kids spell increasingly difficult words aloud. Spelling bees originated in the 19th century as educational contests, promoting literacy and vocabulary skills.

The National Spelling Bee, held annually since 1925, draws contestants nationwide and often surprises outsiders due to English’s tricky spelling rules.