Route 66 turns 100 this year. And while plenty of highways have celebrated a centennial with tasteful ribbon-cutting ceremonies and respectful museum plaques, the Mother Road is doing it differently. It’s doing it with a 30-foot tall astronaut holding a rocket, a smiling blue whale parked next to a pond in Oklahoma, and ten Cadillacs buried nose-first in a Texas cow pasture. Because here’s the thing about Route 66: it was never really about getting somewhere. It what was always about stopping for the ridiculous attractions on the side of the road, grabbing a photo, and wondering aloud, “Who on earth decided to build that?”
So in honor of 100 wild years, here are just 15 of the most gloriously weird, wonderful, and completely unmissable roadside stops along America’s most theatrical highway. Pack your camera and head out on the Mother Road.
Top Attractions to Visit Along Route 66 for its 100th Anniversary
Ceremonial Sign for the 100th Anniversary
A new ceremonial sign as part of the 100th anniversary was revealed earlier this year outside Harry Caray’s Tavern at Navy Pier. Installed in March, this ceremonial sign is intended to be permanent, although it doesn’t replace the historical. However, the Navy Pier location is inherently safer for photo opportunities than the historic beginning at East Adams Street and Michigan Avenue. That’s because only authorized vehicles are allowed on the pier, while the historic start in the heart of the Chicago Loop is always busy with street traffic. What’s more, this new sign makes Route 66 a pier-to-pier pathway, eventually ending at Santa Monica Pier in California. After taking your photos, make sure to visit Harry Caray’s Tavern, founded by the beloved broadcaster Harry Caray, who spent 16 glorious years with the Chicago Cubs.
The Traditional Route 66 Begin Sign – Chicago, Illinois
Every great adventure needs a proper starting gun. Yours is a modest metal sign at the corner of East Adams Street and Michigan Avenue in Chicago. It’s not exactly the Eiffel Tower. In fact, it’s easy to walk right past it. However, it’s right across the street from the Art Institute of Chicago, one of of the city’s premier attractions This little sign — humble, slightly scuffed and frequently passed by tourists — is the portal to 2,400 miles of beautiful weirdness.
The Gemini Giant — Wilmington, Illinois
About an hour south of Chicago, a 30-foot fiberglass spaceman stands guard at its most recent location in Wilmington’s South Island Park. While he has been watching over Route 66 travelers since 1965, his original location was outside the Launching Pad, a restaurant no longer in business. Despite its new location, the Gemini Giant is one of Route 66’s most beloved “Muffler Men”. In other words, it is a category of giant fiberglass advertising figures that proliferated across American roadsides in the 1960s. His story got even better recently: after a dramatic auction, a local museum rescued him from an uncertain fate and returned him to the city. Furthermore, a brand-new souvenir shop called The Landing Pad opened steps away in 2025, making this one of the freshest stops on the entire route.
The World’s Largest Catsup Bottle — Collinsville, Illinois
Yes, catsup. Not ketchup. And yes, it matters.
Standing 170 feet tall on the edge of Collinsville, this former water tower was built in 1949 by the Brook’s Catsup company and is now a beloved National Register of Historic Places inductee. It is, objectively, a giant bottle of condiment. It is also, subjectively, magnificent. The locals are so devoted to it that a volunteer group formed specifically to restore and preserve it. Additionally, they throw a catsup festival in its honor every summer. America contains multitudes.
The Route 66 Red Rocker — Fanning, Missouri
In 2008, a man named Danny Sanazaro decided the best way to attract customers to his feed store was to build a 42-foot steel rocking chair. Naturally, Guinness certified it as the world’s largest. Then a taller rival in Casey, Illinois dethroned it in 2015. Undeterred, Fanning simply repainted the chair fire-engine red and renamed it the Route 66 Red Rocker. Furthermore, it was originally built to actually rock — until safety concerns got in the way, which feels like a very Route 66 story.
Gary’s Gay Parita — Ash Grove, Missouri
The original Gay Parita Sinclair station opened in 1930, named by founder Fred Mason after his wife, Gay. It burned to the ground in 1955 and sat forgotten for decades. Then, in the early 2000s, a Route 66 obsessive named Gary Turner bought the property, tracked down vintage photos, and rebuilt it from scratch — antique pumps, period signage, classic cars out front, and all. Gary became one of the most beloved figures on the Mother Road, greeting every traveler with a story and a warm handshake. He passed away in 2015, but his daughter and her partner carry on his mission with the same hospitality. Furthermore, the station earned a new generation of fans in 2023 when it appeared as the backdrop for Chappell Roan’s “HOT TO GO!” music video. It doesn’t sell gas anymore. What it sells is something far better.
Cars on the Route — Galena, Kansas
Kansas gets just 13 miles of Route 66 — the shortest stretch of any state on the highway. But those 13 miles punch well above their weight, thanks largely to a restored 1934 Kan-O-Tex service station on the north end of Galena’s Main Street. Pixar director John Lasseter and animator Joe Ranft stopped here during a Route 66 research road trip and spotted a rusty old International Harvester tow truck sitting out front. That truck became Tow Mater. Today the station operates as a cafe and gift shop, and the famous tow truck — complete with cartoon eyes added by the owners for the unimaginative — still holds court out front. Furthermore, a handful of other Cars characters have joined him over the years, turning the parking lot into a pilgrimage site for families and Pixar obsessives alike. Even if you’ve never seen the movie, this place is a genuine delight.
The Blue Whale of Catoosa — Catoosa, Oklahoma
There is an 80-foot smiling blue whale on a pond just outside of Tulsa. It has been there since 1972. A man named Hugh Davis built it as a surprise anniversary gift for his wife, Zelta, who collected whale figurines. The whale eventually became a neighborhood swimming hole. Then it became a Route 66 icon. Now it’s one of the most photographed things in the state of Oklahoma. The Blue Whale asks nothing of you. It simply sits there, grinning into the Oklahoma sky, radiating an energy that can only be described as “structurally sound whimsy.” Furthermore, the pond around it still has a certain lazy, summer-afternoon quality that makes you want to stay far longer than you planned. Give in to that feeling. You’re on vacation.
Totem Pole Park — Foyil, Oklahoma
Between 1937 and 1961, a retired teacher named Ed Galloway spent his free time building the world’s largest totem pole in his backyard. Standing 90 feet tall and covered in hand-carved figures, it’s surrounded by a folk art environment of smaller poles, a fiddle-shaped building, and sculptures spread across an entire 9-acre park.
Ed worked entirely alone. He used an estimated 28 tons of cement, 6 tons of steel, and 100 tons of sand and rock. As a result, Totem Pole Park is perhaps the most extraordinary labor of love on the entire highway — and it barely gets the recognition it deserves. Pull over. Spend an hour here. Tell your friends.
Related: Famous Stops Along the Mississippi Blues Trail
Cadillac Ranch — Amarillo, Texas
Ten Cadillacs. Buried nose-first. Tilted at the same angle as the Great Pyramid of Giza. Spray-painted by thousands of visitors since 1974. Located in what appears to be an actual working cow pasture just off I-40.
Cadillac Ranch was created by an art collective called Ant Farm, and it was always meant as a commentary on American car culture. Over the decades, however, it has transcended any single interpretation and become something entirely its own — part art installation, part pilgrimage site, part community canvas. Additionally, this centennial year brings special events to the Ranch, with organizers inviting travelers to add their mark in honor of 100 years of Route 66. Bring spray paint. The cars will tell you what to do.
The U-Drop Inn — Shamrock, Texas
Pull into Shamrock, Texas, and prepare to do a double-take. The U-Drop Inn — also known as Conoco Tower Station — looks like a spaceship landed in the Texas Panhandle sometime around 1936 and just never left. The building’s sweeping Art Deco towers and cantilevered canopies are so striking that it inspired the design of Ramone’s House of Body Art in the Pixar film Cars. Today, the U-Drop Inn operates as a visitor center and is one of the most photographed buildings on the entire route. Furthermore, it’s a reminder that even a gas station can be a work of art when someone cares enough to think about it.
Blue Swallow Motel – Tucumari, New Mexico
Tucumcari, New Mexico has its charms, but none quite as dazzling as the Blue Swallow Motel at dusk. That’s when the original 1939 neon sign flickers to life — a cascade of teal, aqua, and coral that turns the parking lot into something out of a fever dream about the American Southwest. The Blue Swallow is one of the last surviving classic motor courts on Route 66, with individual garages attached to each room and original mid-century furnishings preserved throughout. As a result, staying here doesn’t feel like a nostalgia exercise — it feels like the real thing. Book a room. Sleep under neon. Thank us later.
Wigwam Motel — Holbrook, Arizona
Here is a sentence you can say sincerely in Holbrook, Arizona: “I slept in a giant concrete teepee last night, and it was excellent.” The Wigwam Motel — one of only two surviving Wigwam Villages in the country — consists of 15 individual rooms shaped like 28-foot teepees, arranged in a semicircle around a central office. It was built in the 1950s and is now listed on the National Register of Historic Places. Moreover, the grounds are decorated with vintage cars and Navajo-style murals that make the entire property feel like a postcard from another era. It is kitschy, yes. It is also genuinely charming. It’s also one of the most photographed attractions along Route 66.
Standin’ on the Corner Park — Winslow, Arizona
In 1972, the Eagles released “Take It Easy,” which contained one of rock music’s most indelible opening lines. Winslow, Arizona — mentioned in that lyric — responded the way any self-respecting small town would: by building a park dedicated entirely to that moment. Standin’ on the Corner Park features a life-size bronze statue of a hitchhiker, a painted mural of a girl in a flatbed Ford, and the general energy of a town that knows exactly what it’s famous for and has fully committed to leaning into it. Additionally, the surrounding shops and cafes are genuinely good. Consequently, this becomes one of those stops where you arrive expecting five minutes and leave an hour later, slightly sunburned and humming.
Roy’s Motel and Cafe — Amboy, California
Somewhere in the middle of the Mojave Desert, a 50-foot neon boomerang sign rises out of the heat shimmer and beckons you off the highway. That’s Roy’s — and it has been doing exactly that since 1938. Roy and Velma Crowl built it as a simple gas station, but by the 1950s the complex had grown to include a cafe, a garage, and a motel, with the town of Amboy booming to a population of 700. Then Interstate 40 opened in 1972, bypassed the town entirely, and practically overnight Amboy went silent. Today Roy’s is a hauntingly beautiful time capsule. The reception building is a stunning example of Googie architecture — all swooping angles and mid-century optimism — and the neon sign is best photographed at dusk when the desert sky turns purple behind it. The motel cabins sit empty, the cafe is a gift shop, and the whole place hums with a cinematic stillness. Moreover, it is one of the most photographed spots on Route 66, and one look will tell you exactly why.
Santa Monica Pier — Santa Monica, California
You made it. The Pacific Ocean is right there. The pier stretches out over the water, and a sign on the end of it reads “End of the Trail.”
Now, is the Santa Monica Pier technically a theme park, a fishing wharf, a tourist attraction, and a carnival rolled into one? Yes. Is the Ferris wheel visible from miles away? Yes. Is the whole thing slightly overcrowded and wonderfully chaotic? Absolutely. But that chaos is earned. You’ve driven past fiberglass giants, cave-dwelling outlaws, smiling whales, buried Cadillacs, and giant condiment bottles to get here. The pier, in all its loud, salt-sprayed, funnel-cake-scented glory, is the perfect final act.
Take a breath. Look back east. Somewhere out there, a 30-foot tall astronaut in Illinois is watching over everything.
Your Route 66 Centennial Cheat Sheet
The full drive covers roughly 2,400 miles from Chicago, Illinois to Santa Monica, California. Most road-trippers complete it in 10 to 14 days, though two weeks is far more comfortable for anyone who intends to actually stop at everything. And based on this list, you definitely intend to stop at everything.
Best time to go: If you can resist the urge to travel sooner, fall (September–October) is best for mild temperatures across all eight states. On the other hand, summer works well through Illinois and Missouri, although it gets brutal in Texas and Arizona, so plan accordingly.
The golden rule: Stay off the interstate whenever possible. The magic of Route 66 lives on the old alignments, the frontage roads, and the downtown main streets — not in the bypasses that tried to make it all disappear.
The Mother Road is 100 years old, and it still knows exactly how to throw a party. All you have to do is show up.
For a full calendar of Route 66 Centennial events in 2026, visit the Route 66 Centennial Commission.
Related: Your Guide to Celebrating America’s 250th Anniversary
About The Author
Randy Yagi is an award-winning writer who served as the National Travel Writer for CBS from 2012 to 2019. More than 900 of his stories still appear in syndication across 23 CBS websites, including New York, Los Angeles, Chicago, and San Francisco. During his peak years with CBS, Randy had a reported digital audience reach of 489 million and 5.5 million monthly visitors. Additionally, his stories have appeared in the Daily Meal, CBS News, CBS Radio, Engadget, NBC.com, NJ.com, and Radio.com. He earned a Media Fellowship from Stanford University and is a Bay Area Travel Writers (BATW) member.