There’s something almost magnetic about Route 66. Maybe it’s the promise of wide-open roads, or the way vintage neon signs seem to whisper stories from another era. This iconic stretch of American highway has been calling road trippers since 1926, and honestly, that call hasn’t gotten any quieter.
Your grandmother might have driven it. Your favorite movie probably featured it. But here’s what matters: Route 66 is still here, still thrilling, and still packed with quirky stops that’ll make your Instagram feed jealous and your soul a little fuller.
Whether you’re planning your first cross-country adventure or you’re a seasoned traveler looking for that perfect mix of nostalgia and novelty, you’re going to want to know where to stop. Because trust me, there’s a big difference between just driving the Mother Road and actually experiencing it.
Best Places to Visit Along Route 66
From bizarre roadside attractions that’ll make you laugh out loud to natural wonders that’ll leave you speechless, Route 66 serves up an incredible variety of stops. Here are ten places that absolutely deserve a spot on your itinerary.
1. Cadillac Ranch, Amarillo, Texas
Picture this: ten Cadillacs buried nose-first in the ground, their tail fins pointing at the Texas sky like some kind of automotive Stonehenge. That’s Cadillac Ranch, and it’s exactly as wild as it sounds.
What makes this place special isn’t just the sight itself. It’s what you get to do there. Bring spray paint. Seriously. Visitors are encouraged to tag the cars, which means the installation is constantly changing, constantly evolving. The Cadillacs are buried in layers upon layers of paint now, creating this incredible texture that feels almost organic.
You’ll find it just west of Amarillo, sitting in a wheat field off Interstate 40. The best part? It’s free. Park in the dirt lot, walk across the field, and add your mark to history. Go at sunset if you can. The way the light hits those paint-covered cars creates shadows and colors that photographers dream about. Plus, there’s something quietly profound about standing there as the sun goes down, surrounded by this art installation that’s been collecting stories since 1974.
2. Santa Monica Pier, California
This is where Route 66 officially ends, and what an ending it is. The Santa Monica Pier juts out over the Pacific Ocean, giving you that satisfying sense of completion after 2,448 miles of driving.
But here’s what most people don’t realize until they get there: the pier itself is an experience. The historic carousel has been spinning since 1922. The Pacific Park amusement park brings a carnival atmosphere, complete with a solar-powered Ferris wheel that lights up the night. You can grab fish tacos, watch street performers, or just lean against the railing and watch the waves roll in.
Look for the “End of the Trail” sign. Everyone takes a photo there, and you should too. There’s no shame in being a tourist at a place this iconic. After that, walk down to the beach. Take your shoes off. Feel the sand between your toes and the Pacific breeze on your face. You’ve earned it.
3. Blue Whale of Catoosa, Oklahoma
You’re driving through Oklahoma, and suddenly a massive blue whale is sitting in a pond. Your first thought might be, “What on earth?” Your second thought should be, “I need to see this up close.”
Hugh Davis built this 80-foot whale in the early 1970s as an anniversary gift for his wife. She collected whale figurines, so naturally, he built her a giant one she could swim inside. The logic is impeccable. The pond was his private swimming hole, but eventually, he opened it to the public, and families came from all over to swim through the whale’s mouth.
These days, you can’t swim there anymore, but you can walk around, climb on the whale, and soak in the pure oddness of it all. The blue paint is bright and cheerful against the Oklahoma landscape. Local volunteers maintain the site now, keeping this piece of roadside Americana alive for future generations. It’ll take you maybe 20 minutes to see everything, but those 20 minutes will put a smile on your face that lasts for miles.
4. Meramec Caverns, Missouri
Drop underground, and you’ll find one of Route 66’s most spectacular natural attractions. Meramec Caverns has been a tourist draw since the 1930s, and the moment you step inside, you’ll understand why people have been coming here for generations.
The guided tours take you through massive chambers filled with stalactites, stalagmites, and formations that look like frozen waterfalls. The guide will point out shapes: an elephant, a wine table, and curtains of stone. Some of the formations are millions of years old, growing one drop of water at a time. There’s a seven-story mansion formation that’ll make your jaw drop. The Stage Curtain, a massive flowstone formation, regularly appears on lists of the world’s most impressive cave features.
The temperature inside stays at a comfortable 60 degrees year-round, which makes it a perfect escape on a hot summer day. The tour lasts about 80 minutes, and yes, there are some stairs involved, but it’s absolutely worth the effort. Fun historical note: Jesse James allegedly used these caverns as a hideout. Whether that’s true or tourist marketing doesn’t really matter when you’re standing in a chamber that feels like nature’s cathedral.
5. Wigwam Motel, Holbrook, Arizona
Sleep inside a concrete teepee. That’s the pitch here, and it’s delivered exactly as promised. The Wigwam Motel is one of the last surviving wigwam motels from the chain that once dotted Route 66, and staying here is like stepping into a time capsule.
Each wigwam is a separate unit, arranged in a semicircle around the parking lot. Inside, you’ll find restored vintage furniture, original hickory wood pieces, and modern amenities that keep things comfortable without ruining the retro vibe. The bathrooms have been updated, thank goodness, but the spirit of mid-century motor lodge travel remains intact.
The best time to photograph the wigwams is early morning or evening when the light is soft and the shadows are long. The owners have maintained this place with obvious love and attention to detail. Classic cars often park in front of the units, adding to the vintage atmosphere. Book ahead because these 15 wigwams fill up fast, especially during peak travel season. There’s something magical about waking up inside a concrete teepee, walking outside into the Arizona morning, and knowing you’re part of a tradition that’s been going strong since 1950.
6. Petrified Forest National Park, Arizona
This is where Route 66 and serious natural beauty collide. Petrified Forest National Park sits right along a historic alignment of the highway, and it’s unlike anywhere else you’ll visit on your trip.
We’re talking about trees that turned to stone 225 million years ago. Walk the trails, and you’ll see logs that look like they were cut yesterday, except they’re solid rock, often sparkling with quartz crystals. The colors are unreal: reds, purples, yellows, blues. Nature created these patterns through a process of mineral replacement that took millions of years.
But the petrified wood is just part of the story. The Painted Desert sprawls across the northern section of the park, offering views of badlands that shift color throughout the day. Visit the Puerco Pueblo to see petroglyphs left by ancestral Puebloan people. Stand on the edge of the Blue Mesa and feel very small against geological time.
Budget at least three hours here, though you could easily spend a full day. The park entrance fee is reasonable, and it grants you access to multiple viewpoints, trails, and the visitor centers. Bring water. Arizona doesn’t joke around with its heat, and the high desert environment can be deceptive. This stop elevates your Route 66 trip from quirky road adventure to something approaching spiritual.
7. Gateway Arch, St. Louis, Missouri
The Gateway Arch rises 630 feet above St. Louis, and it’s visible from miles away. This stainless steel monument catches the light differently throughout the day, sometimes gleaming silver, sometimes glowing gold, always commanding attention.
You can ride to the top in small pod-like trams that travel up the inside of the arch’s legs. It’s a bit claustrophobic, sure, but the view from the top is worth any momentary discomfort. You’ll see the Mississippi River, the city sprawling in all directions, and on clear days, you can see for miles into Illinois.
The grounds around the arch have been beautifully redesigned in recent years, creating a park that connects the arch to the riverfront. There’s a museum underneath that tells the story of westward expansion, complete with exhibits about the people who made the journey. The whole complex is a National Park Service site now, which means park rangers who actually know their stuff and can answer your questions with real depth.
Go early in the day if you can. Lines for the tram get long, especially in summer. Security screening is required, so plan accordingly. Standing underneath this marvel of engineering, looking up at how it seems to defy gravity, you’ll feel that sense of American ambition and possibility that makes Route 66 trips so compelling.
8. Oatman, Arizona
This old mining town sits in the Black Mountains, and it feels like you’ve driven onto a movie set. False-front buildings line the narrow main street. Wild burros wander around looking for handouts. And yes, there are staged gunfights in the street on weekends.
Oatman boomed during the gold rush and nearly became a ghost town when the mines closed. But Route 66 saved it, and now tourism keeps it alive. The burros are descendants of pack animals used by miners, and they’ve been here so long they’re protected. You can buy food for them at local shops, and they’re remarkably friendly, if occasionally stubborn about posing for photos.
The road through Oatman twists and climbs through the mountains, offering stunning views and more than a few white-knuckle moments. This stretch of original Route 66 isn’t for nervous drivers, but it’s absolutely one of the most scenic portions of the entire highway. Cool Creek Canyon on the approach is particularly beautiful.
Walk into the Oatman Hotel, where Clark Gable and Carole Lombard spent their wedding night. The walls are covered in dollar bills, a tradition that started decades ago and now numbers in the thousands. Grab a cold drink, chat with locals, and soak in the atmosphere of a place that refuses to let go of its history.
9. Chain of Rocks Bridge, Illinois
This bridge doesn’t carry traffic anymore, and that’s exactly what makes it special. Chain of Rocks Bridge crosses the Mississippi River just north of St. Louis, and it’s been converted into a bike and pedestrian path that offers one of the most unique experiences on Route 66.
The bridge has a 22-degree bend in the middle. When it was built in 1929, this was the solution to an engineering challenge, but now it creates this surreal moment where you’re walking across the Mississippi and suddenly the bridge just turns. It’s disorienting and delightful.
On the Illinois side, you’ll find the old Chain of Rocks water intake towers rising from the river like castles. The views from the middle of the bridge are spectacular. You can see downtown St. Louis in the distance, the river flowing below, and on both sides, the landscape stretches out in ways that remind you how big this country really is.
The bridge is maintained by a non-profit organization, and it’s free to visit. Bikers love this spot, but even if you’re not on two wheels, it’s worth parking and taking the walk. Just be aware that it’s about a mile across, so budget your time and energy accordingly. There’s something peaceful about being on a bridge that no longer has to rush, that now exists just to let people pause and look around.
10. Ted Drewes Frozen Custard, St. Louis, Missouri
Let’s end with something sweet. Ted Drewes has been serving frozen custard in St. Louis since 1929, and the line of customers wrapping around the building proves that some things just work.
This isn’t ice cream. Frozen custard is richer, denser, and made with eggs that give it this incredible silky texture. But what Ted Drewes is really famous for is the “concrete.” Order one, and they’ll blend your chosen toppings into the custard so thoroughly that they can turn the cup upside down without anything falling out. It’s a party trick that never gets old.
The Route 66 location (there are two Ted Drewes shops) sits right on old Chippewa Street, and on summer evenings, the parking lot becomes a gathering place. People eat their concretes leaning against their cars, families spread out on the picnic tables, and this sense of community feels increasingly rare.
The menu is overwhelming in the best way. Dozens of flavors and toppings. First-timers usually go for a classic like the Turtle (caramel, pecans, fudge) or the Hawaiian Delight (pineapple, cherries, cashews). The portions are generous. Even a small one will probably be more than you expect.
What makes Ted Drewes a true Route 66 stop isn’t just the food, though the custard is legitimately excellent. It’s the way this place has remained essentially unchanged for decades, the way it still draws crowds without any gimmicks or modern marketing, just the simple promise of something delicious made the right way. That’s the spirit of Route 66 in a cup.
Wrapping Up
Route 66 permits you to slow down, to take the scenic route, to stop at places that make you smile for no particular reason. These ten spots represent just a fraction of what’s out there waiting for you, but they’re an excellent start.
Pack your car with good music, comfortable shoes, and a sense of adventure. Leave room in your schedule for unexpected detours because the best Route 66 stories often come from the places you didn’t plan to stop. This highway has been inviting people to hit the road for nearly a century, and your turn is now.
