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.

1

Ohio: Birthplace of aviation

Image: History in HD

Ohio proudly claims the title "Birthplace of Aviation," being the home state of the Wright brothers. While the first successful flight actually took place in North Carolina, above the sand dunes of Kitty Hawk, most of the brothers' ideas were first developed back in their bicycle shop in Dayton, Ohio.

Their achievement made headlines worldwide, and soon the brothers secured their first military contract for the aircraft that would become the first practical airplane sold commercially. As symbols of American ingenuity, these two Ohioans are remembered for their innovative spirit and determination to succeed—qualities central to the Midwest spirit.

2

Michigan: Freshwater coast

Image: Jeff DeWitt

Michigan is home to the largest freshwater coastline in the United States, thanks to its proximity to four of the five Great Lakes. This vast "unsalted" coast is a crucial part of America’s natural heritage. In fact, Michigan has the highest percentage of water area among all states, with a whopping 41.5% of its surface covered by water!

Its 3,288 miles of freshwater shoreline offer stunning scenery and numerous recreational opportunities, making it a popular destination for tourists. As part of the nation's natural legacy, the Great Lakes also serve as a vital resource, providing freshwater and transportation for neighboring states and industries.

3

Wisconsin: Dairyland legacy

Image: Josh Turner

As the nation’s leading producer of cheese and other dairy products, Wisconsin is rightly known as "America’s Dairyland." Furthermore, the Badger State's dairy industry dating back to the 19th century, is deeply intertwined with its cultural and economic identity.

The commitment of Wisconsin's farmers to quality and innovation has made the state a cornerstone of American agriculture. Wisconsin cheese, renowned for its variety and excellence, is a staple of the American diet, enjoyed by millions across the nation.

4

Illinois: Land of Lincoln

Image: Naomi August

Illinois is often referred to as the "Land of Lincoln," honoring its deep connection to Abraham Lincoln, one of America’s most revered presidents. Though Lincoln was actually born in Kentucky, he spent his formative years in Illinois.

It was here that he began his political career and developed the ideals that would guide the nation through its most challenging period. Illinois honors Lincoln’s legacy through numerous monuments and the Abraham Lincoln Presidential Library and Museum, which houses the largest collection of Lincoln-related documents and artifacts in the world.

5

Indiana: Racing capital

Image: Andrew Roberts

Indiana is home to the Indianapolis Motor Speedway, the world-famous venue for the Indy 500, a race that epitomizes America’s love for speed, engineering, and sportsmanship. Since its inaugural race in 1911, the Indy 500 has been a symbol of innovation and endurance.

These racing events are a key part of the region's identity, attracting hundreds of thousands of spectators annually, both nationally and internationally. Interestingly, the Indianapolis Motor Speedway is also one of the largest sports venues in the world, with a seating capacity of over 250,000.

6

Minnesota: The land of 10,000 lakes

Image: Laura Kessler

Minnesota, known as the "Land of 10,000 Lakes," actually boasts over 11,000 lakes, making it a paradise for outdoor enthusiasts and a cornerstone of America’s biodiversity. The state's unwavering commitment to preserving these natural wonders has made these lakes a vital resource for both native wildlife and tourism.

The Boundary Waters Canoe Area, a wilderness area with over 1,000 pristine lakes, is one of the most visited natural attractions in the United States, drawing nearly 150,000 visitors annually. These lakes also play a crucial role in supporting diverse ecosystems, providing habitats for over 200 species of birds and countless other wildlife.

7

Missouri: The gateway to the West

Image: Intricate Explorer

The Gateway Arch in St. Louis, Missouri, stands as a monumental symbol of America’s westward expansion and the pioneering spirit that built the nation. Located at the site of St. Louis's founding in 1764, on the west bank of the Mississippi River, the towering monument was designed by Finnish-American architect Eero Saarinen and completed in 1965.

The 630-foot-tall arch represents the "gateway to the West," honoring the daring pioneers who ventured into the unknown to expand the nation’s borders. The Gateway Arch is also the tallest man-made monument in the United States and is part of the Jefferson National Expansion Memorial, which commemorates not only the pioneers but also the Louisiana Purchase—a key moment in America's territorial expansion.

8

Kansas: America’s breadbasket

Image: Josh Redd

Often called the "Breadbasket of America" due to its vast wheat production, Kansas's wheat fields are a cornerstone of American agriculture, feeding millions both in the United States and around the world. With its rich, fertile plains, the state has been a major agricultural hub since the 19th century.

Kansas consistently ranks among the top wheat-producing states in the country, contributing approximately 15% of the total U.S. wheat supply. Other leading crops include alfalfa, hay, oats, barley, and corn. This significant output supports not only domestic food production but also exports to international markets, making Kansas a key player in global food security.

9

Iowa: First-in-the-Nation Caucuses

Image: Clay Banks

The Iowa caucuses have been the starting point for presidential campaigns since 1972, often setting the tone for the national race. This unique role gives Iowa outsized influence in American politics, as candidates focus their early efforts on winning over the state’s voters.

Although caucus-goers may not fully represent the nation’s overall demographics, the Iowa caucuses are still seen as a strong indicator of a candidate’s potential performance in subsequent contests. Candidates who perform poorly in the Iowa caucuses frequently drop out in the following days.

10

South Dakota: Mount Rushmore

Image: Nils Huenerfuerst

Mount Rushmore, located in South Dakota, is one of the most iconic symbols of American history, featuring the carved faces of four U.S. presidents. Completed in 1941, Mount Rushmore celebrates the leadership and vision of Presidents George Washington, Thomas Jefferson, Theodore Roosevelt, and Abraham Lincoln.

This monumental sculpture represents the nation’s ideals and the enduring legacy of its leaders. Carved into the Black Hills, the granite faces on Mount Rushmore each measure about 60 feet tall. No wonder the entire project took 14 years to complete! Nowadays, the site attracts over 2 million visitors annually, making it a central landmark in American cultural heritage.

1

Waterpark Capital of the World, Wisconsin Dells

Image: Kenny Eliason

Waterparks are a funny thing. Adults go there almost exclusively to take their kids, but end up enjoying themselves, sometimes even more than the younger ones. Self-proclaimed as the " Waterpark Capital of the World ," Wisconsin Dells offers fun and adventure for kids and the aforementioned kids at heart.

Its multiple resorts include Noah’s Ark, the largest outdoor waterpark in the world, The Wilderness Resort, which has the largest indoor-outdoor combination, Bigfoot Ziplining, The Original Wisconsin Ducks, Devil’s Lake State Park, boat tours, spas, golf courses, casinos and much more.

2

City of Big Shoulders, Chicago

Image: Sawyer Bengtson

The Windy City needs no introduction but no Midwestern treasures list would be complete without mentioning it. As the Midwest's largest metropolitan area, Chicago is a popular option for a weekend getaway. It houses numerous parks, including ones with lakefront beaches, or iconic sculptures like "The Bean."

Its incredible architecture is best viewed from the water during a river cruise or while boating on Lake Michigan. Its virtually i nfinite food options , ranging from Greek to Mexican to Polish, and its world-class museums , make for a must-visit.

3

Museum City, Kansas City

Image: gilber franco

Sitting on the state line between Missouri and Kansas, the City of Fountains has a vast assembly of museums ready to be discovered by visitors from all over the world.

From local landmarks like the Nelson-Atkins Museum of Art, boasting an impressive collection of over 34,000 pieces and 5,000 years , the National WWI Museum and Memorial, The Negro Leagues Baseball Museum, to the newly renovated Harry S. Truman Presidential Library and Museum, this city has it all.

4

Ozarks Lake, Missouri

Image: K. Mitch Hodge

Long before the TV series of the same name, the Ozarks was a region famous for its natural beauties, entertainment opportunities, and multiple cuisine options. This expansive reservoir with more than 1,100 miles of shoreline has spots like Lake of the Ozarks State Park, Bridal Cave, and various restaurants and resorts.

And if the water activities are not your thing, you can visit the links at one of several golf courses or enjoy a day of wine tasting on the Lake of the Ozarks Wine Trail.

5

Wining and dining, Traverse City

Image: Pablo Merchán Montes

Traverse City may be famous for its slices of pie and tart cherries, which can be found at farm stands across the Up North region through late summer. But it has much more to offer its visitors.

Acres of wineries and orchards all along the Leelanau and Old Mission peninsulas' rolling hills are complimented by the Lake Michigan scenery and the nearby Sleeping Bear Dunes National Lakeshore. And, when the summer season is over, the Traverse City area also boasts enviable skiing terrain, fat-tire bike trails, and snowmobile routes , making it an attractive destination for winter recreation.

6

Hiking paradise, Duluth

Image: Tom Gainor

This Minnesotan city located on the shores of Lake Superior is an ideal spot for a weekend getaway. Visitors of the Canal Park area can bike or walk along the Lakeway , a nearly 8-mile path that follows the shoreline, take pictures of the Aerial Lift Bridge , and explore local art galleries .

Travelers can also tour all 39 rooms at Glensheen, a historic estate built in the early 1900s, or book a first-class ticket in a domed train car on the North Shore Scenic Railroad. And, when hunger strikes, Duluth boasts a generous selection of lakeside eateries and breweries.

7

Family trip favorite, Omaha

Image: Andrew Seaman

Whether you are into history, nature, arts, or the food scene, Omaha has it all. And, with attractions like the Omaha Children's Museum and the Henry Doorly Zoo and Aquarium , this city is a great choice for a family trip.

The Durham Museum is a great place for history buffs, the Lauritzen Gardens Botanical Center has an impressive collection of plants flowers, and trees, and its noteworthy restaurants and bars attract culinary visitors from around the world.

8

Black Hills National Forest, South Dakota

Image: Frank Thiemonge

The amazing Black Hills National Forest can be found at the western edge of South Dakota, where a small mountain range is surrounded by 1.2 million acres of protected wilderness, making it a haven for outdoor activities.

Visitors of the Black Hills can hike, bike, ride horses, rock climb, and visit the Mount Rushmore National Memorial , which features giant mountainside busts of four American presidents.

9

Small-town charm, Mackinac Island

Image: leah hetteberg

If you are looking for a holiday destination with no cars or chain hotels and, instead, horse-drawn carriages and bed and breakfast accommodations in family-owned hotels , Mackinac Island might be the place you are looking for. Located between Michigan's Upper and Lower peninsulas, this Lake Huron island beckons to visitors who want to relax and unwind.

Mackinac Island State Park occupies most of the island, providing visitors with countless opportunities to enjoy outdoor activities like hiking, biking, horseback riding , and a variety of eateries serving everything from American classics to its famous fudge.

10

Prince’s legendary Paisley Park Studios, Minneapolis

Image: DJ Johnson

The former home and recording studio of the "Purple Rain" composer is located outside of Minneapolis in Chanhassen, Minnesota. Prince built Paisley Park back in 1987 and lived here until he died in 2016.

His Royal Badness himself requested that his home be open to the public after his death and now fans can tour the complex and see the studio where he recorded some of his biggest hits and the soundstage where he rehearsed for tours.