1

Charm City

Image: Girish Dalvi

Even with this nickname, this coastal spot wasn’t always known for its good looks . In fact, back in the '70s, it was struggling with a bit of an image problem. For that reason, a creative PR campaign worked some magic and gave it a nickname that stuck. Now it’s known for its iconic seafood and working-class roots. Oh, and locals are seriously proud of their blue crab dishes. This nickname has a certain sparkle to it, don’t you think?

2

The Bayou City

Image: Nicole Herrero

Think steamy summers, sprawling highways, and a whole lot of swampy waterways. This nickname may sound like it belongs in Louisiana, but don’t be fooled. It’s a nod to the bayous that weave through this massive southern city. It’s also a hub for space travel, energy, and some top-notch food. If you know the South, this one should ring a bell. Have you guessed it already?

3

The Big D

Image: JosephHershMedia

Everything’s bigger in Texas, and this city wears its size with swagger. The nickname itself is bold and simple: Just one big letter. It brings up images of cowboy boots, shiny buildings, and football fever. This place is known for business, barbecue, and a whole lot of bravado. You know the state, but do you know which Texas titan we’re talking about?

4

The Golden City

Image: IRa Kang

Between the shimmering water, a world-famous structure, and a "bright" past, this place practically glows. Its nickname is short and shiny, much like the hills it rests upon. Known for quirky charm and tech power, it’s a city where history and innovation collide. And yes, the fog does roll in, but somehow it just adds to the magic. Got it yet?

5

Rip City

Image: Edgar Chaparro

This one’s a bit of a curveball… Yes, we’re referencing basketball here because this nickname started as a throwaway comment during a basketball game in the '70s, but it stuck like glue. Now you’ll see it on jerseys, bumper stickers, and maybe even a tattoo or two. It doesn’t make a lot of sense, but that’s part of the charm. Sports fans, this one’s for you!

6

Beantown

Image: Xuancong Meng

Baked beans might not sound glamorous, but they sure helped this historic place earn a nickname. That and a long list of American "firsts," this city is wonderful. It’s also been known to call itself the "Hub of the Universe." Has anyone seen modest? History buffs and chowder lovers, you’re probably already picturing cobblestone streets, aren’t you?

7

Baltimore

Image: Brendan Beale

Yep, Charm City is Baltimore! That catchy name was cooked up to shine a brighter light on the city’s best features. And guess what? It worked! Baltimore’s got a rich mix of culture, grit, and pride, plus some of the best crab cakes you’ll ever taste. Not bad for a city once overlooked, right?

8

Houston

Image: Carlos Delgado

Say hello to The Bayou City: Houston! Its unique geography inspired the nickname, and the city’s grown into a powerhouse of space exploration, culture, and business. Between NASA connections and a killer food scene, Houston has more going for it than just the heat. And yes, those bayous are still winding through it all.

9

Dallas

Image: Gabriel Tovar

That big old D? Dallas, of course. This city isn’t shy about its size or influence, and the nickname says it all. From skyscrapers to stadiums, Dallas lives large and wild. Add the cowboy flair, and you’ve got a Texas city that owns its identity. We love it!

10

San Francisco

Image: Alexey Komissarov

The Golden City? None other than San Francisco, what else could it be? With its iconic Golden Gate Bridge and a history rooted in gold rush dreams, it’s an easy one to guess. But even beyond the sparkle, the city has got a heart of tech and a soul of protest. Yes, the fog is quite the character, but this city shines bright anyway.

11

Portland

Image: Zack Spear

If you guessed Rip City was Portland, you guessed right! The name came out of a Trail Blazers game and somehow became a token of pride. That’s Portland for you: a little weird, totally charming, and full of surprises.

12

Boston

Image: todd kent

You guessed it: Beantown is Boston. The beans are just the beginning—Boston is packed with revolutionary charm, Ivy League brains, and a sports scene like no other. And if you hear someone call it "The Hub," now you know what they mean. It might just be the center of the universe after all.

1

Tipping is expected, not optional

In the U.S., leaving a tip is considered part of the cost of the meal, not a bonus . Diners typically add 15 to 20 percent to the bill, especially in full-service restaurants.

This practice exists because many servers earn lower base wages and depend on tips. In many other countries, service charges are already included in the bill, making the American system feel unusual or even confusing.

2

Free refills are the norm

Many American restaurants offer unlimited refills on soft drinks, iced tea, and coffee . Once you order a beverage, it often keeps coming at no extra cost.

Elsewhere, each drink is typically billed separately, and refills are rarely free. For visitors to the U.S., this can feel surprisingly generous compared to their dining experiences at home.

3

Ice comes with everything

In the U.S., drinks are often served filled with ice, whether it’s soda, water, or even juice . It’s considered a refreshing standard, especially in warmer climates.

In many other countries, ice is used sparingly or avoided altogether. Some people prefer drinks at room temperature, making the American preference for ice stand out immediately.

4

Portions are huge

American restaurant portions are known for their size. Many meals are large enough to serve more than one person or to provide leftovers for later .

In contrast, other countries tend to serve smaller, more balanced portions. The American approach reflects a culture of abundance, but it can be unexpected for first-time visitors.

5

Taking leftovers home is typical

Asking for a take-home container, also known as a "doggy bag," is a normal part of dining in the U.S. Restaurants are prepared for it, and many people expect to leave with leftovers.

In some countries, this practice is less common or even discouraged. The American "doggy bag" reflects both larger portion sizes and a practical approach to reducing food waste.

6

Waiters check in frequently

In the U.S., servers often return to the table several times during a meal . They may ask how everything tastes, refill drinks, or check whether anything else is needed.

While meant to be attentive, this can feel intrusive to foreign visitors. In many other cultures, less interruption is preferred, and diners typically signal the server only when necessary.

7

Customizing your order is normal

In the U.S., it's common to request changes to a dish, such as removing ingredients or adding extras . Restaurants are usually flexible and expect these requests.

In other parts of the world, altering a menu item may be frowned upon. The American habit reflects a strong emphasis on personal choice and individual preferences.

8

Tap water is served automatically

In American restaurants, a glass of tap water is often brought to the table without being requested . It is typically free and refilled throughout the meal.

In many other countries, bottled water is the default and must be ordered separately.

9

Meals tend to move quickly

Dining in the U.S. often follows a faster pace. Food arrives quickly, and the bill may be brought shortly after the meal is finished .

In contrast, in many other cultures, meals are meant to be long, relaxed experiences. The American approach reflects efficiency and a faster daily rhythm.

10

Splitting the bill is common

In the U.S., restaurants commonly allow separate checks , making it easy for each person to pay their share. This is especially helpful in group settings.

In many other countries, splitting the bill can be more complicated or is actively discouraged. The American system emphasizes convenience and individual responsibility at the table.

11

Sweet foods are common at breakfast

Breakfast in the U.S. often includes sweet items such as pancakes, waffles, pastries, or cereal, alongside eggs, bacon, and toast. Syrup and sugar are common additions at the start of the day.

In many other countries, breakfasts tend to be exclusively savory, featuring foods like bread, cheese, or eggs. The American preference for sweetness can feel like a treat to visitors.

12

Dining is generally casual

While there are many exceptions at five-star, fine dining establishments, American dining culture is typically relaxed, with fewer formal rules about dress or behavior . People often eat out in casual clothing and informal settings.

In other countries, meals, especially dinner, can be more formal events. The American style reflects a focus on comfort rather than tradition.

1

122 S. Michigan Ave.

Image: Allen Boguslavsky

Why not start the trip at the place where it all began? For Route 66, the beginning is right in the heart of Chicago , at 122 S. Michigan Ave. Look for the iconic pylon near the intersection of South Michigan Avenue and East Adams Street.

Fun fact: the Mother Road didn’t always start there. Back in 1926, Jackson Boulevard at Michigan Avenue was the official launch point for travelers!

2

Gateway Arch

Image: Intricate Explorer

Follow your adventure in St. Louis with the Gateway Arch, a towering 630-foot tribute to westward expansion. This stainless-steel beauty isn’t just a landmark, it’s an experience in itself.

Ride the tram to the top for jaw-dropping views of the Mississippi River and the city skyline. It’s the perfect way to set the tone for the rest of your journey.

3

Route 66 Drive-In Theater

Image: Tim Mossholder

Ready for some vintage vibes? Swing by the Route 66 Drive-In Theater in Carthage, Missouri. This blast from the past offers double features under the stars , just like in the good old days.

Opened in 1949, closed in 1985, and re-opened in 1998, this drive-in theatre has functioned ever since and plays two movies from Friday to Sunday every single week. Bring your lawn chairs and a cooler, or cozy up in your car for the full retro experience.

4

The Golden Driller

Image: Jametlene Reskp

Now it’s time to meet the Golden Driller, a 76-foot-tall oil worker who’s been standing proud in Tulsa, Oklahoma, since the 1960s.

It’s one of the largest freestanding statues in the country and a nod to Oklahoma’s rich oil history. At the base, there’s a sign that reads: "The Golden Driller, a symbol of the International Petroleum Exposition. Dedicated to the men of the petroleum industry who, by their vision and daring, have created from God’s abundance a better life for mankind." Strike a pose with this gentle giant, and you’ll feel downright tiny.

5

Route 66 Museum

Image: Carol Highsmith's America

For the following stop, you can take a break to explore the Oklahoma Route 66 Museum in Clinton. In it, you’ll be able to see artifacts, photos, and exhibits celebrating the history of the Mother Road.

Wander through rooms themed by decade, and you’ll feel like you’re traveling through time. From the Dust Bowl to the heyday of diners, this museum paints quite a vivid picture of Route 66’s golden era. And, of course, you can go by the gift shop to get a road trip memento.

6

Cadillac Ranch

Image: Heidi Kaden

If you’ve ever wanted to graffiti a Cadillac, this is your chance. Cadillac Ranch in Amarillo, Texas, features 10 half-buried cars sticking nose-first out of the ground. It’s an open-air art installation that’s as weird as it is wonderful.

Grab a can of spray paint (provided by friendly locals or your fellow travelers) and leave your mark. Just be warned, it might only last a day before someone else paints over it!

7

Route 66 Halfway Point

Image: Vicky McLain

Welcome to Adrian, Texas, the official halfway point of Route 66! You’re 1,139 miles from both Chicago and Los Angeles, so take a breath and celebrate!

The MidPoint Café is famous for its "ugly crust" pies. Don’t trust the name; they are actually delicious! It’s a perfect pit stop to recharge and think about the fact that you’ve conquered half of the Mother Road. Only halfway to go!

8

Meteor Crater

Image: John Ballem - a collection of personal photos

Arizona is home to some magical attractions, and Meteor Crater is no exception. This massive impact site, located near Meteor City, was created by a meteorite over 50,000 years ago . Standing on the rim and peering into the 560-foot-deep crater, you’ll feel like a tiny speck in the universe. The visitor center has some cool exhibits on space and meteors, which is perfect for science lovers or anyone who likes their roadside stops with a side of awe.

9

Old Trails Bridge

Image: Jimmy Whitson

Crossing the Colorado River into Arizona, the Old Trails Bridge in Topock is a picturesque reminder of Route 66’s early days. Though it’s no longer open to traffic , it’s a popular photo spot for travelers.

The rusted steel beams and sweeping desert views will give you a beautiful moment. Pause here, take in the history, and imagine the countless cars that once went across its span.

10

Burger Hut

Image: Haseeb Jamil

Needless, California, may be small, but it’s big on charm, especially at Burger Hut. This unassuming little eatery is beloved for its old-school burgers, fries, and milkshakes. It’s the kind of place where the food is made with love , and the portions are hearty. Don’t take our word for it; just go try it!

After hours on the road, there’s nothing better than a juicy burger and a chance to stretch your legs. This spot is a gem along Route 66!

11

Hollywood sign

Image: Scott Greer

As you approach the end of Route 66, why not take a detour to see the world-famous Hollywood Sign? Perched on the hills overlooking Los Angeles, it’s a symbol of dreams and stardom .

Take a hike to the best viewpoints for some exercise (and epic photos, of course). Sure, it’s a bit off the beaten path, but what’s a road trip without a side quest?

12

Santa Monica Pier

Image: Joel Mott

You’ve made it! The Santa Monica Pier marks the official end of Route 66 . With its iconic Ferris wheel, arcade games, and ocean views, it’s the perfect spot to celebrate completing your journey.

Now you’re done, dip your toes in the Pacific, grab a cone of soft-serve, and reflect on all the memories you’ve made along the way. The Mother Road may end here, but the stories you’ve collected will last a lifetime.