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.

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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.

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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.

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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

Monkey's Eyebrow, Kentucky

Image: Jonny Belvedere

A name like "Monkey's Eyebrow" begs an explanation. One assumes there is a very particular story behind it. This is an unincorporated community in Ballard County, rural Kentucky, and the origin of its name is disputed. One of the theories suggests that, when seen from the air or on a map, the landscape in Ballard County looks like a monkey’s head, and this community has formed where the eyebrow would be .

Kentucky is, after all, no stranger to towns with odd names. Some of them include Rabbit Hash, Bachelor’s Rest, Sparta, and Oddiville itself.

2

Whynot, North Carolina

Image: Tammi Nowack

Yet another unincorporated community with an unusual name is Whynot, from Randolph County, North Carolina. Founded in the 18th century, the name was originally spelled separately: "Why Not."

The legend holds that, undecided about what name to pick for the town, the residents started throwing at one another "Why not this?" and "Why not that?" Until one bored resident said: "Why not name the town ‘Why Not’ and let's go home?" Joke or not, that ended up being the official name for the land. Today the community has an estimated 100 inhabitants.

3

Fries, Virginia

Image: Dzenina Lukac

One would expect a big monument of golden fries to be erected in some square within Fries, Virginia. But you would be misled to imagine that. When pronounced correctly, this town’s name rhymes with "breeze." Situated on the New River in Grayson County, Virginia, Fries boasts beautiful natural landscapes, and visitors are encouraged to bike, hike or horse ride around the unspoiled countryside.

The town was named after a prominent cotton mill owner and businessman, Francis Henry Fries. Fries holds music festivals annually and has a strong bluegrass and country music culture.

4

Canadian, Texas

Image: Cedric Fauntleroy

Canadian, Texas is not, in fact, Canadian. Founded in 1887, it is home to around 2,400 residents from the north of Texas, in Hemphill County. It was named after the Canadian River that flows one mile north. The river is a tributary of the Arkansas River, and it was named so in the 1820s when Canadian traders were spotted camping in its borders.

Here is a piece of trivia that you would never guess: The beginning and the end of the movie Cast Away (2000), with Tom Hanks, which occur in Texas, were filmed in Canadian and nearby.

5

Truth or Consequences, New Mexico

Image: Csongor Schmutc

A city with a name that sounds like a threat, Truth or Consequences, New Mexico, is within Sierra County and has a population of a little over 6,000. It is sometimes shortened to "T or C."

The place wasn’t always called this.

Originally, it was named Hot Springs, after the springs it was built over, belonging to the Artesian Basin. However, in 1950, the NBC Radio quiz show called "Truth or Consequences" declared that the 10th anniversary of the program would be recorded in the first town that changed its name to that of the show. Thus, Hot Springs officially became Truth or Consequences to gain the honor, and the show’s host visited the former Hot Springs yearly for half a century after that.

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Dinosaur, Colorado

Image: Danny Grizzle

Dinosaur is a small town in Moffat County, Colorado, that was once called "Artesia." However, in the 1960s, it was decided to rename it to attract tourists who were traveling to see the Dinosaur National Monument, east of the town. The park contains over 800 archeological sites and unique fossils and was proclaimed a National Monument in 1915 by Woodrow Wilson.

Dinosaurs did once roam the golden fields under the Blue Mountain Range where Dinosaur sits. Beyond the visit of paleontology fans, the town prides itself on boasting stunning natural views and wildlife that includes deer, elk, and antelope.

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Okay, Oklahoma

Image: STEPHEN POORE

Those who named this Oklahoma town "Okay" weren’t just trying to be funny. Okay, OK had several other names throughout history, including Coretta, Falls City, and Rex. The current one was adopted in 1919. Oklahoma Auto Manufacturing Company had a factory nearby, makers of the "O.K. Trucks." The official postal designation was changed in its honor.

The community had been established in 1806 on the east bank of the Verdigris River and had soon become a trading post for many visitors in the area, which allowed the settlement to grow.

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Uncertain, Texas

Image: Scott Graham

Imagine the complications of filling out a form indicating that the name of your city is "Uncertain." This probably has happened to several residents, and it is closely related to the origin story of the town’s name.

It is said that, when applying for township, the residents hadn’t yet agreed on a name for the place. They tried to explain this by writing "uncertain" in the form’s blank space for the town name, hoping to resolve it in the future. But the township was eventually granted and the place came to officially be called Uncertain.

Uncertain is located in eastern Texas very near to the border with Louisiana. It sits near the Big Cypress Bayou and the banks of Caddo Lake.

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Cut and Shoot, Texas

Image: Guðleifur Kristjánsson

The town of Cut and Shoot, Texas, got its unusual name from a confrontation that occurred in July 1912. A local church, meant to be shared by various denominations, became the center of conflict when an Apostolic preacher was invited to hold a meeting. The community split into two sides, those for and against the preacher's appearance, and both arrived armed to enforce their stance.

During the argument, a frightened eight-year-old boy exclaimed, "I'm going to cut around the corner and shoot through the bushes!". The conflict was resolved peacefully that day, but a trial unfolded between the two leading families. When the judge asked the name of the community, someone suggested calling it the place of the "cutting and shooting scrape." Residents eventually took a liking to this term and adopted it.

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Coward, South Carolina

Image: Yohan Marion

"Coward" sounds like an accusation, but it is also the name of a town in Florence County, South Carolina, with a population of just over 700. One would expect its name to derive from some story of dishonor and shame, but Coward is instead just a surname .

It is unclear and disputed whether the town was named after Capt. Solomon Coward, who owned most of the land, Col. Asbury Coward, a Confederate veteran, or John Wilson Coward, a member of the "Committee of 50." However, the rural farming community was called that many years before it was incorporated in 1963.

1

Bright colors

Image: Yaritza

In the 80s, neon was absolutely everywhere, and let’s be honest, it was very hard to miss. Found in clothes, accessories, makeup, signs, and posters, blindingly bright colors became a new style statement. From hot pink to acid green, neon yellow to electric blue, this color palette could be found in pop culture, on the streets, and everywhere in between.

2

Bold fashion

Image: cottonbro studio

There's only one word to describe 80s fashion: bold . B old hair, bold accessories, bold colors, bold everything! Fashion during this decade was strongly influenced by pop music and new rock subgenres such as New Wave. For the first time, different styles began to mix, combining formal garments with rebellious accents —like pairing suits with sneakers, mind you. Whether it was shoulder pads, multicolored leg warmers, or those striking Miami Vice suits, fashion in the 80s was all about vibrancy and an aura of success.

3

Big hair, strong makeup

Image: Gustavo Cerati, Public domain, via Wikimedia Commons

In the 80s, crazy cuts and dramatic makeup became an everyday thing, a way of expressing one’s personality and style everywhere you went. From musicians like Madonna to leading ladies like Demi Moore or Julia Roberts, the stars led the way with their perms, pumped-up hair volume, tanned faces, and bright eyeshadows.

But let's not forget the guys! They also introduced the iconic mullet, popularized by celebrities like Rod Stewart, tennis player Andre Agassi, and Patrick Swayze, just to name a few.

4

Rise of yuppie culture

Image: MART PRODUCTION

In a nutshell, Yuppie culture was characterized by slicked-back hair, V-neck sweaters, and a condescending attitude. The term yuppie , an acronym for "young urban professional," emerged in 1980 in an article in Chicago magazine. It described a young person in their 20s or 30s who was part of the middle to upper class, a socioeconomic group that became the forefront of the decade.

From the beginning, this label sparked divided opinions: For some, it represented ambition and success; for others, it symbolized superficiality, an excessive materialism, and an apparent superiority complex. Accurate or not, the trend eventually faded away after the 1987 Wall Street Crash.

5

Toys on TV

Image: cottonbro studio

The 1980s were marked by spending Saturday mornings watching ads on cartoon commercial breaks. How did this happen? From this decade onwards, companies were finally allowed to market directly to kids. The result was hundreds of all kinds of toy ads. They advertised everything from creative games like the Rubik's Cube or Lego to cute and cuddly toys like Care Bears and My Little Pony. This era also saw the beginnings of the must-have toy trend, with Cabbage Patch dolls leading the pack.

6

Music on the go

Image: cottonbro studio

During the 80s, it was common to see people walking down the street with a Walkman on their hips or a boombox to their ears. Although the boombox gained popularity in the 70s, it became mainstream in the 80s thanks to hip-hop and breakdancing culture. Yet, the Walkman would soon steal its thunder. This revolutionary new audio player allowed people to bring their music with them anywhere without bothering everyone around. And that’s also how mixtapes became a thing!

7

Personal computers

Image: Tomas Martinez

The 80s were a prominent decade for electronics development. In 1981, IBM introduced its first personal computer, and everyday life and work would never be the same again. More affordable computers were created thanks to the introduction of powerful, smaller, and cheaper processors, reaching a wider audience and creating greater demand. Models such as the IBM PC, the Commodore 64, and the Apple Macintosh became household names, paving the way for the era of domestic computing.

8

Rise of video games

Image: cottonbro studio

Thanks to technological advances in graphics and gameplay over the decade, video games finally became undeniably popular. With the rise of arcade machines and home consoles, a series of iconic games managed to capture the attention of a wider audience, igniting a cultural phenomenon that would influence music, film, and television. Titles such as Super Mario Bros., The Legend of Zelda, Space Invaders, Pac-Man, and Donkey Kong became classics that defined an era.

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Cable TV goes mainstream

Image: Coline Haslé

When cable TV hit the mainstream, it not only gave the big three American networks a run for their money, but it also allowed the world access to specialized shows that better suited their tastes. Whether your interest was sports, comedy, or music, cable had something for everyone.

CNN and HBO definitely changed television forever, but it was perhaps MTV that left the most indelible mark by offering greater insight into contemporary bands and musicians via live performances and music videos.

10

Fitness fever

Image: Ron Lach

The 1980s were the golden age of fitness, a trend that reflected society's growing interest in health and wellness. Exercise routines were not just a workout, but a cultural phenomenon that turned our living rooms into mini gyms.

Major clothing brands began designing exercise-specific apparel and accessories, such as leotards, crop tops, and headbands. Celebrities also capitalized on the fitness craze. Jane Fonda, for example, became a massive hit in 1982 with her iconic workout videos, some of the best-selling VHS of all time.