While Chicago and Los Angeles mark the famous endpoints of Route 66, this classic American highway holds countless stories between its start and finish. The 2,448-mile stretch winds through small towns and desert landscapes, offering road-trippers a chance to experience the heart of America away from interstate highways and busy cities.
From roadside diners that have served travelers since the 1930s to quirky museums and local mom-and-pop shops, here are 19 must-see stops along Route 66 that showcase the real charm of this historic road.
Chicago, Illinois
Start your epic Route 66 journey in Chicago, where the “Mother Road” begins at the corner of Michigan Avenue and Adams Street. Head to the iconic Millennium Park to snap photos at the reflective Cloud Gate sculpture (aka “The Bean”) before diving into the city’s famous deep-dish pizza scene at Lou Malnati’s or Giordano’s. For the best views of the cityscape, visit the 360 CHICAGO observation deck on the 94th floor of the former John Hancock Center, where you can sip cocktails while looking out over Lake Michigan. Don’t leave without trying a Chicago-style hot dog at Portillo’s – just remember the cardinal rule: no ketchup allowed.
St. Louis Gateway Arch, Missouri
Standing tall on the banks of the Mississippi River since 1965, the Gateway Arch has become the defining symbol of St. Louis and the American westward expansion. The 630-foot stainless steel monument rises from the Jefferson National Expansion Memorial Park, where the city first took root as a humble trading post. Visitors can ride the unique tram system to the top, where windows offer views stretching 30 miles in each direction across the river and city. Down below, the recently renovated museum tells stories of Native Americans, pioneers, and the builders who crafted this engineering marvel. At sunset, the arch’s metallic surface catches the light in a way that makes it seem to glow from within, creating a silhouette that’s been photographed millions of times but still stops people in their tracks.
Meramec Caverns, Missouri
Ever wondered what lies beneath the famous Route 66? Deep in Missouri’s heartland, Meramec Caverns offers a fascinating peek into the underground world that shaped America’s geology. These limestone caves, once used as a hideout by Jesse James and his gang, now welcome visitors to explore their winding passages and natural formations. You can take guided tours through the well-lit chambers, learning about the cave’s rich history while admiring ancient mineral deposits that took millions of years to form. The caverns stay at a comfortable 60 degrees year-round, making them a perfect pit stop during hot summer road trips along the Mother Road.
Oklahoma City, Oklahoma
Take a trip down memory lane in Oklahoma City, the largest city along Historic Route 66. Walk through Bricktown, the city’s entertainment district, where former warehouses now house restaurants, shops, and a mile-long canal perfect for water taxi rides. Stop by the National Cowboy and Western Heritage Museum to dive into the Old West, or catch a Thunder game at the Paycom Center if you’re visiting during basketball season. For a moving experience, visit the Oklahoma City National Memorial, which honors those affected by the 1995 bombing. Don’t miss the chance to try local favorites like chicken fried steak at Cattlemen’s Steakhouse, a Route 66 institution since 1910.
Cadillac Ranch, Amarillo, Texas
About 30 minutes west of downtown Amarillo stands one of Route 66’s most peculiar roadside attractions. At first glance, Cadillac Ranch looks like a bunch of old cars randomly stuck nose-first into a dusty Texas field. And that’s exactly what it is – ten vintage Cadillacs buried at the same angle as the Great Pyramids of Giza. Created in 1974 by an art collective called the Ant Farm, this oddball installation has become a must-stop spot where visitors bring spray paint to leave their mark on the cars. The graffiti-covered Caddies change color almost daily as new layers of paint build up, making each visit a different experience. Don’t forget to bring your own can of spray paint – adding your personal touch to this iconic piece of American pop art is part of the tradition.
Painted Desert, Arizona
Take a detour off Route 66 to explore the Painted Desert, a natural wonder that stretches across 93,500 acres of Arizona. This colorful landscape features bands of red, orange, and purple rocks that look like they’ve been painted by an artist’s brush. You can drive through Painted Desert National Park or stop at one of the eight overlooks for sweeping views of the multicolored badlands. For the best experience, visit during sunrise or sunset when the changing light creates beautiful shadows across the desert hills. Pack a picnic lunch and enjoy it at one of the designated areas, or take a short hike on the Painted Desert Rim Trail to get a closer look at the remarkable rock formations.
Petrified Forest National Park, Arizona
Have you ever seen a 225-million-year-old tree turned to stone? That’s exactly what you’ll find at Petrified Forest National Park, where ancient fallen trees have crystallized into rainbow-colored fossils scattered across the desert landscape. Located along Route 66 in eastern Arizona, this otherworldly park lets you step back in time to when dinosaurs roamed the earth. You can explore the painted desert badlands, discover Native American petroglyphs at Newspaper Rock, and walk among the largest collection of petrified wood on earth. The park’s Blue Mesa trail offers an easy way to get up close to these natural wonders, while the historic Painted Desert Inn provides a glimpse into the park’s Route 66 heyday.
Grand Canyon National Park, Arizona
The first time you catch sight of the Grand Canyon, it hits you like nothing else – this massive gorge carved by the Colorado River stretches as far as your eyes can see. At 277 miles long and up to 18 miles wide, it’s a place that makes you feel wonderfully small against nature’s handiwork. While most visitors stick to the South Rim’s well-worn paths, the adventurous souls who venture deeper are treated to a maze of colorful rock layers, hidden waterfalls, and quiet corners where you can soak in the desert silence. It’s not just a quick photo stop – plan to spend at least a day exploring the rim trails, watching the shadows play across the canyon walls, and maybe even hiking down into its depths if you’re up for the challenge.
Route 66 Ghost Town, Oatman, Arizona
A detour through Oatman, Arizona takes you deep into one of Route 66’s most authentic ghost towns from the 1920s gold rush era. Situated in the Black Mountains of Mohave County, this former mining boomtown now welcomes visitors with its wooden boardwalks and wild burros roaming freely through the dusty streets. The descendants of pack animals left behind by old miners still patrol the town daily, eagerly accepting carrots from tourists passing through. Historic buildings like the Oatman Hotel, where Clark Gable and Carole Lombard allegedly spent their honeymoon night, stand as reminders of the town’s prosperous past. Mock gunfights still break out in the streets at high noon, while local shops housed in original structures sell everything from Route 66 memorabilia to the town’s famous handmade ice cream.
Santa Monica Pier, California
Looking for the perfect end to your Route 66 adventure? The Santa Monica Pier marks the iconic highway’s western terminus, where the Mother Road meets the Pacific Ocean. This century-old wooden pier, jutting out into the sparkling waters of Southern California, offers classic amusement park thrills at Pacific Park, complete with a solar-powered Ferris wheel that lights up the night sky. You can cast a line with local fishermen, catch street performers entertaining crowds, or simply watch the sun dip into the ocean while munching on cotton candy. It’s also home to the official “End of Trail” sign, where road-trippers gather daily to snap photos and celebrate completing their cross-country journey.
Albuquerque Old Town, New Mexico
Tucked along historic Route 66, Albuquerque’s Old Town has been the heart of New Mexico’s largest city since 1706. The neighborhood spreads out from its central plaza, where adobe buildings and hidden courtyards tell stories of Spanish colonial history. Local artists sell their turquoise jewelry and woven blankets from small shops that line the narrow streets, while the scent of green chile and fresh tortillas drifts from nearby restaurants. San Felipe de Neri Church, built in 1793, watches over the plaza as it has for centuries, its thick walls and twin bell towers a testament to the area’s rich cultural heritage. Visitors can wander through more than 100 shops, galleries, and restaurants that make this five-block historic district a perfect stop for anyone seeking authentic New Mexican charm.
Pops Soda Ranch, Arcadia, Oklahoma
Of all the quirky stops along Route 66, Pops Soda Ranch in Arcadia, Oklahoma stands out as a true roadside gem. This modern-day soda shop boasts a massive 66-foot LED-lit soda bottle out front, making it impossible to miss – especially at night when it glows against the prairie sky. Inside, you’ll find walls lined with over 700 different types of sodas, from classic root beers to oddball flavors like bacon and ranch dressing. It’s not just a pit stop, but a playful museum of fizzy drinks where road trippers can sample their way through America’s soda-making history. The attached restaurant serves up classic diner fare, perfect for taking a break from the highway and watching other travelers marvel at the bottle collection.
Blue Whale of Catoosa, Oklahoma
Ever heard of an 80-foot-long blue whale lounging by the side of a highway? That’s exactly what you’ll find in Catoosa, Oklahoma, where this quirky roadside attraction has been making drivers do a double-take since 1972. Created by Hugh Davis as an anniversary gift for his wife (who collected whale figurines), this concrete sea creature comes complete with a water slide that once emptied into a swimming pond. While you can’t swim there anymore, the Blue Whale has become a beloved Route 66 landmark where visitors can climb inside the whale’s head, peek through its eyes, and snap photos on its tail. The surrounding picnic area makes it a perfect pit stop to stretch your legs and embrace the offbeat charm that made Route 66 famous.
Chain of Rocks Bridge, Illinois
Dating back to 1929, the Chain of Rocks Bridge stretches across the Mississippi River connecting Illinois and Missouri along the historic Route 66. While many travelers come for the bridge’s unique 22-degree bend in the middle, the spot also serves as a prime location for watching river barges navigate the intense rapids below. The mile-long bridge, now reserved for pedestrians and cyclists, offers views of the old water intake towers rising from the river and makes an ideal spot for sunset photos. Though no longer carrying cars, the bridge remains one of the most recognizable landmarks along Route 66, and visitors can access it from either the Illinois or Missouri side throughout the year.
Meteor Crater, Arizona
Located along historic Route 66 in northern Arizona, Meteor Crater first caught my eye back in 2019. This massive depression in the earth’s surface spans nearly a mile wide, carved out roughly 50,000 years ago when a meteorite crashed into the desert floor. The rim rises 150 feet above the surrounding plains, while the bowl plunges 550 feet deep into the ground. From the visitor center perched on the crater’s edge, you can peer down into this otherworldly sight, where astronauts once trained for moon missions in the 1960s. The rugged hiking trails around the rim offer views across the crater floor, which could easily fit 20 football fields side by side.
Santa Fe, New Mexico
Step back in time when you visit Santa Fe, the oldest capital city in the United States. The city’s adobe buildings and winding streets tell stories from centuries of Native American, Spanish, and Mexican influences. Walk through the Plaza, a historic gathering place since 1610, where local artisans sell handmade jewelry and traditional crafts. For authentic New Mexican cuisine, head to The Shed, tucked away in a 300-year-old hacienda, where the red chile enchiladas will make your taste buds dance. It’s the perfect place to experience the charm of the American Southwest.
Williams, Arizona
Ever wondered what it’s like to step back in time to the heyday of Route 66? Williams, Arizona lets you do just that. Known as the “Gateway to the Grand Canyon,” this small town was the last Route 66 community to be bypassed by Interstate 40. Today, its main street is lined with neon signs, classic diners, and authentic 1950s memorabilia that transport you straight back to the golden age of American road trips. You can hop aboard the Grand Canyon Railway for a scenic ride to the South Rim, or spend your evening at Bearizona Wildlife Park, where black bears and wolves roam freely in their natural habitat just outside your car window.
Hackberry General Store, Arizona
Ever driven past an old-school general store that looks frozen in time? That’s exactly what you’ll find at Hackberry General Store, a quirky pit stop that’s been serving Route 66 travelers since 1934. This rustic shop in the Arizona desert feels like stepping into a time capsule, with vintage gas pumps, classic Coca-Cola signs, and an impressive collection of Route 66 memorabilia covering every inch of wall space. You can browse through nostalgic souvenirs, snap photos with retro cars parked outside, and chat with friendly locals who share stories about the Mother Road’s glory days. The store even keeps its original wooden shelves stocked with classic road trip snacks and cold drinks – perfect for those long stretches of desert driving.
Cars on the Route, Galena, Kansas
Stop by Cars on the Route in Galena, Kansas, and you’ll find yourself at one of Route 66’s most charming pieces of movie history. This former gas station turned tourist spot is where you’ll meet the real-life inspiration for Tow Mater from the Pixar film “Cars” – a rusty 1951 International boom truck that caught the eye of the movie’s creators. Like many places along the Mother Road, this spot tells a story of both preservation and reinvention, with friendly local owners who love sharing tales about the highway’s golden age. The old service station’s weathered exterior and collection of vintage vehicles transport you right back to the days when Route 66 was America’s main street connecting Chicago to Los Angeles.