When Route 66 was created in 1926, no one could have imagined that it would become the coolest stretch of highway on the U.S. map. The original idea was simple: Americans needed an easy way to head west, and this took them from Lake Michigan to the Pacific Ocean.
Soon after the “Mother Road” opened, tasty diners, fun hotels, and quirky pit stops popped up in small towns and big cities along the way, and a century of great American road trips followed.
While the 2,448-mile stretch has changed a bit since its inception, it’s still one of America’s most iconic road trips. The route today is dotted with iconic stops that hearken back to the golden age of car travel: bold neon signs that flicker to life at dusk, diners full of homemade pies and oddball attractions that pretty much force you to pull over and take a photo.
Take, for instance, The Gateway Arch in St. Louis, Missouri, which is the country’s tallest monument, or a 66-foot soda bottle soaring roadside in Ree Drummond’s home state of Oklahoma. From The Art Institute of Chicago to the Santa Monica Pier, Route 66 is peppered with such landmarks and one-of-a-kind attractions, making it well worth the long drive.
In honor of its centennial birthday, this itinerary highlights some of the coolest pit stops in eight states across America. So many of them are like a step back in time—you’ll feel like you’re driving right into a vintage postcard. Read on and enjoy the ride!
Plan your next adventure:
- American Towns with Views That Take Your Breath Away
- The Most Scenic Drives Across the Country
- These Family Vacations Are Fun for All Ages
Illinois
First stop: Illinois. Every Route 66 adventure starts in downtown Chicago before winding through charming small towns, vintage diners, and playful attractions across the Prairie State. Whether you’re embarking on a full cross-country journey or exploring this certain stretch of highway, these attractions deserve a visit!
Route 66 Begin Sign
Chicago
Since this historic sign marks the start of Route 66, you’ll definitely want to snag a photo underneath it! You can even make a day of it by exploring The Art Institute of Chicago.
The Art Institute of Chicago
Chicago
This renowned museum is home to famous paintings including Edward Hopper’s Nighthawks, Georges Seurat’s A Sunday on La Grande Jatte, and Grant Wood’s American Gothic.
Lou Mitchell’s
Chicago
This family diner on Jackson Boulevard has been around even longer than the highway. Fuel up on coffee and pancakes or one of its famous doughnut holes, which have been served since 1958.
Gemini Giant
Wilmington
In the 1960s, this “Muffler Man” statue popped up to celebrate America’s space race and draw customers to a nearby restaurant. The quirky name was decided in a contest among schoolchildren!
Ambler’s Texaco Gas Station
Dwight
You can’t buy gas here anymore, but it’s still worth a stop. The restored 1930s gas station, named after its longtime manager Basil “Tubby” Ambler, now serves as a visitors’ center.
Cozy Dog Drive In
Springfield
Legend has it, corn dogs on a stick were introduced to the world here, and they’re still made with the batter recipe developed by original owner Ed Waldmire in 1946! These days, Ed’s grandson is in the kitchen.
Henry’s Rabbit Ranch
Staunton
Back in the day, if you stopped here for information or souvenirs, you’d find rabbits hopping around the property. This summer, you’ll find Volkswagen Rabbits in their place!
Missouri
From the country’s tallest monument to one of the oldest operating drive-in theaters, Missouri has so much to offer along its stretch of Route 66. You can even break up your trip by getting your frozen custard fix!
Gateway Arch
St. Louis
This 630-foot stainless steel rainbow, often called “The Gateway to the West,” is the tallest monument in the country. Buy tickets ahead of time for a tram ride to the top.
Ted Drewes Frozen Custard
St. Louis
This family-owned frozen custard shop has been a staple in St. Louis since 1929. Pull over to order the “Concrete,” a shake so thick, it’s served upside down!
Meramec Caverns
Stanton
This miles-long collection of caves, created from eroding limestone deposits, helped Missouri earn its nickname “The Cave State.” Bring a jacket: It’s a constant 58 degrees.
Munger Moss Motel
Lebanon
Rooms were $3 a night when this iconic motel opened in 1946. You can’t stay here now, but you can stop to see the famous neon sign.
66 Drive-In Theater
Carthage
Pull into a parking spot at dusk to experience one of the last original drive-in theaters on Route 66. If you stay for a double feature, you’ll see a nostalgic trailer during intermission!
Kansas
Kansas might be the shortest Route 66 state, but it’s packed with old-fashioned appeal. This stretch of roads crosses the southeastern corn of the state, so you’ll travel through the towns of Galena, Riverton, and Baxter Springs. If you’re a fan of the beloved Pixar movie Cars, be sure to check out the real-life inspiration for one of the main characters.
Cars on the Route
Galena
The creators of Cars stopped at this service station and saw a rusty tow truck that inspired Mater from the movie. The original is still here for photo ops.
Nelson’s Old Riverton Store
Riverton
Established in 1925, this general store is one of the oldest operating businesses along Route 66. Step inside for candy, soda, sandwiches, and souvenirs.
Marsh Rainbow Arch Bridge
Riverton
One of the last surviving bridges of its kind, Marsh Rainbow Arch Bridge is a historic landmark that offers a glimpse into the history of highway engineering and building.
Historic Downtown
Baxter Springs
Make a stop by Baxter Springs. Its historic buildings and quaint shops give you a taste of small-town life on the Mother Road.
Baxter Springs Station
Baxter Springs
Back in the day, this 1930s gas station was the perfect place to fuel up for a road trip. Today, the restored station is a reminder of the highway’s prime.
Oklahoma
The portion of Route 66 that cuts through The Pioneer Woman’s home state is jam-packed with unique tourist attractions. Think: the world’s largest concrete totem pole, an 80-foot-long whale, and a 66-foot-tall soda bottle. Each one is basically made to be photographed!
Totem Pole Park
Foyil
Folk artist Ed Galloway created this collection of about a dozen structures featuring Native American culture and motifs, plus the world’s largest concrete totem pole.
Blue Whale of Catoosa
Catoosa
A giant blue whale is not what you’d expect to find here! A local zoologist built this 80-foot metaland-concrete beast in 1972 as a place for his grandchildren to play. Visit to picnic, fish, and feed the turtles.
Round Barn
Arcadia
Local farmer William Harrison Odor built this structure in 1898 with the idea that if a tornado hit, it would glide around the outside rather than destroy the property. Fortunately, the concept hasn’t been put to the test!
Pops 66
Arcadia
Pull over when you see this 66-foot soda bottle. The combination gas station, restaurant and convenience store has become a popular stop: The shop sells 700 varieties of soda!
Sid’s Diner
El Reno
During the Great Depression, when meat prices were astronomical, Sid’s started offering its famous fried onion burgers: thin beef patties bulked up with a heap of onions.
Oklahoma Route 66 Museum
Clinton
Learn about the history of Route 66 and the people who traveled it at this fun interactive museum. Check out vintage cars, artifacts, signs, and more while you wander through.
Texas
You know what they say: Everything’s bigger in Texas—including its Route 66 attractions! During this stretch of your cross-country journey, you’ll find classic diners, quirky museums, larger-than-life landmarks, and plenty of other significant stops full of old-school charm.
The U Drop Inn
Shamrock
This 1930s Art Deco beauty thrived as a gas station and café during Route 66’s heyday. Today, you can pop inside for a breakfast burrito, a pulled pork sandwich, or a big slice of coconut cream pie.
The Leaning Tower of Britten
Groom
This wasn’t an accident: Ralph Britten intentionally installed his water tower at an angle in the ’80s to grab attention and attract passersby.
Big Texan Steak Ranch
Amarillo
This restaurant poses a famous steak-eating challenge: Can you eat a 72-ounce steak, plus a baked potato, shrimp cocktail, salad and a roll in under an hour? Apparently, 10,000 folks have prevailed!
Cadillac Ranch
Amarillo
Bring a few cans of spray paint with you: The art group Ant Farm came up with the idea to create this interactive exhibit featuring 10 Cadillacs buried nose-first in the Texan dirt.
Midpoint Cafe
Adrian
This eatery earned its name for being exactly halfway along Route 66. Stop in for a burger and a slice of pie, and don’t forget to take a photo at the famous midway sign.
New Mexico
With its wide-open landscapes, adobe architecture, and neon landmarks, New Mexico brings breathtaking beauty and rich culture to Route 66. Every stop will give you a jaw-dropping dose of Western charm and impressive history.
Blue Swallow Motel
Tucumcari
This family-operated motel will take you right back to the glory days of mid-century road trips on Route 66. The rooms are decorated with vintage furniture and accessories, including rotary phones on the nightstands!
Tucumcari Neon Signs
Tucumcari
The buzzing neon signs here make Tucumcari one of the most photographed areas of Route 66: It was home to several neon shops in the mid-1900s. Drive through at night so you can see the whole city aglow.
Blue Hole
Santa Rosa
Take a dip in this crystal-clear natural swimming hole. It’s one of the most popular scuba diving destinations in the country thanks to the consistent 61-degree water and 100-foot-deep visibility. If you’re feeling daring, check out the hidden caves.
Santa Fe Plaza
Santa Fe
Back in 1609, this plaza was founded as a defense location for the Spanish. These days, it’s a gathering place for both locals and visitors who come for the markets, community events and people-watching.
Tinkertown Museum
Sandia Park
This wonder of a museum is full of handmade miniatures and animatronics by folk artist Ross Ward, who started carving figures in 1962. Admire the creativity in the circus, Wild West and old-school Americana scenes.
Arizona
Once you pass the Arizona state line, you’re in for a treat! This Southwestern leg of Route 66 has picture-perfect desert scenery, retro diners and motels that seem to be frozen in time, and quaint towns that you’ll want to explore for hours.
Petrified Forest National Park
via Holbrook
When you visit, you’ll see both the modern landscape and the one that was preserved more than 200 million years ago, with fossilized plants and animals. Stop by the paleo lab or catch a ranger talk to learn more about the fossils.
Wigwam Motel
Holbrook
Stay in one of 15 individual teepees here (incorrectly called wigwams). According to the business deal, the owner of this location, Chester E. Lewis, had to install coin-operated radios in every teepee, and proceeds (in dimes!) went to Redford.
Meteor Crater
via Winslow
This roadside attraction long predates Route 66: The mile-wide crater was formed more than 50,000 years ago when a meteorite hit Earth. Learn about the natural wonder at the museum situated on the north rim.
Area 66 Alien Center
Yucca
Though it looks more like a giant golf ball than a UFO (as far as we know), this roadside alien museum is a fun, quirky pitstop. It sits at the site of an alleged 1953 flying saucer crash.
Wild West Shoot-Outs
Oatman
Step back in time in this tiny Arizona town: You’ll get to see staged shoot-outs, wooden sidewalks and donkeys! They roam the streets freely here; there are more of them than people.
Grand Canyon
via Williams
It’s a bit of a drive from Route 66, but everyone needs to see this: The Grand Canyon is one of the most awe-inspiring natural wonders on earth. Spend some time hiking, biking, rafting and stargazing.
California
As Route 66 crosses into California, the finish line is finally in sight! With antique signs, famous diners, and, of course, the iconic Santa Monica Pier, the final leg of your journey will give you one last unforgettable taste of Americana.
Roy’s Motel & Cafe
Amboy
In 1938, Roy’s Motel & Cafe was the only spot in town where you could get gas, a bed, and a meal. Nowadays, it’s a great spot and photo op for tired travelers.
Amboy Crater
Amboy
This dormant volcano hasn’t erupted in about 10,000 years, so feel free to hike in or enjoy a picnic on a nearby bench. It’s made up of ash and cinders and is known for its symmetrical cone shape.
Elmer’s Bottle Tree Ranch
Oro Grande
A forest in the middle of a desert is hard to believe, but in this case the trees are all made of large metal poles and bottles. Artist Elmer Long built the collection across 2 acres; it includes more than 200 bottle trees.
The Original McDonald’s Museum
San Bernardino
A shrine to McDonald’s, this museum is loaded with symbols of the fast food chain’s past: old packaging, original menus, vintage signs, and a collection of Happy Meal toys.
Santa Monica Pier
Santa Monica
Ah, the symbolic end of Route 66! You’ll feel like a kid again at Pacific Park, where you can ride the Ferris wheel, play arcade games, and eat funnel cake.
Kelsey Hurwitz is the associate features editor for The Pioneer Woman Magazine. When she's not writing about ranch life, home decor and food, she can be found knitting and catching up on her favorite reality TV shows.
Lilly Blomquist is the associate editor at The Pioneer Woman, where she writes lifestyle stories across a wide range of topics—including news, entertainment, holidays, food, and more.
