Thinking of hitting Route 66 in 2025? Now’s the time. The road’s getting close to its 100th birthday, and tons of towns are reviving their retro spirit. From weird roadside attractions to national parks and old-school diners, this route’s packed with stops that are worth your gas money.
This list? It’s the real-deal stuff. No filler. Just 15 must-see places that make a Route 66 trip unforgettable. Get your camera ready and maybe clear out some trunk space for souvenirs you didn’t plan on buying.
Chicago, Illinois
Kick off your trip where it all begins: East Adams Street and Michigan Avenue. There’s a small metal sign that says “Begin Route 66,” and yeah, it’s iconic. Snap your photo early (tourists roll in fast), then grab a deep-dish slice at Lou Malnati’s nearby.
Parking can be tricky downtown, so use a garage app or hop on foot from a nearby train station. If you’ve got time, do an architecture river cruise. Totally worth it before you hit the road.
Wilmington, Illinois
The Gemini Giant is hard to miss. He’s a towering green astronaut standing outside the Launching Pad diner. Route 66’s been known for oddball attractions, and this one nails it.
The diner reopens for the 2025 season with revamped classics and a new visitor center called The Landing Pad. Grab a burger, explore the gift shop, and get that photo. It’s just 60 miles from Chicago, so it’s perfect for your first quirky pit stop.
Pontiac, Illinois
This town LOVES Route 66. Start at the Route 66 Association Hall of Fame Museum. It’s free and full of vintage road signs, old gas pumps, and restored cars. Murals decorate nearly every downtown building, and there’s even a life-size car you can sit in for photos.
Parking is easy and free. For a snack, swing by Lydia’s Cup for coffee or an ice cream cone. Tip: walk the alleyways—they hide some of the best murals in town.
Springfield, Illinois
History nerd or not, Springfield’s Lincoln sites are worth it. The Abraham Lincoln Presidential Library and Museum is super interactive, not just dusty documents. His preserved home is a couple blocks away, and walking tours leave regularly.
Want a quick bite? Grab a horseshoe sandwich at D’Arcy’s Pint (it’s a Springfield thing—fries and cheese sauce galore). If you’re stopping overnight, hotels downtown are walkable and usually under $150.
St. Louis, Missouri
Take the tram up the Gateway Arch. It’s weird and claustrophobic, but the view from 630 feet up? Wild. Book your ride in advance online to skip the lines. The museum underneath is free and really well done.
Afterward, drive about 10 minutes to Ted Drewes for frozen custard. Locals swear by the “concrete.” Pro tip: street parking’s tough near the Arch, so use the Arch Garage (it’s right under the park).
Stanton, Missouri
Meramec Caverns is one of Missouri’s oldest tourist spots, and yes, it’s touristy, but fun. You’ll get a guided, hour-long cave tour filled with dramatic lighting, tall limestone formations, and stories about Jesse James possibly hiding there.
Tours run every 30 minutes. Adult tickets are $25, and it stays a comfy 60°F inside year-round. If you’ve got kids, they’ll love the zipline and climbing wall outside too.
Collinsville, Illinois
It’s a giant ketchup bottle. On a water tower. What more do you need? Built in 1949 for Brooks Catsup, this 170-foot landmark is just off Route 66 and makes for a quick, oddball detour. You can’t go inside it, but there’s a small lot nearby for easy photos.
Best time to visit is late morning when the sun hits just right. Pair this with a pit stop at Old Herald Brewery for lunch nearby.
Eureka, Missouri
This park used to be a town. No joke—Times Beach was evacuated in the ‘80s due to contamination and turned into Route 66 State Park. It’s now a quiet spot with trails, picnic tables, and a visitor center full of Route 66 memorabilia.
Restrooms are open seasonally, and the walking bridge across the Meramec River offers scenic views. It’s a peaceful break between busier cities.
Baxter Springs, Kansas
This stretch in Kansas is short—just 13 miles—but Baxter Springs is the highlight. The Marsh Rainbow Arch Bridge is one of the last of its kind, and it’s a great spot for stretching your legs.
Park nearby and walk across to take in views of Spring River. If you need gas or snacks, downtown has a classic 1920s gas station turned visitor center. It’s small-town charm done right.
Catoosa, Oklahoma
You’re about to meet a giant blue whale. Built in the 1970s as a swimming hole gift (seriously), the Blue Whale of Catoosa is now one of Route 66’s most photographed stops.
You can climb inside its smiling mouth, picnic by the water, or browse the tiny on-site gift shack. Parking’s free, and it’s open daylight hours only. There’s no entry fee—just don’t fall in the pond, lol.
Foyil, Oklahoma
Ed Galloway’s Totem Pole Park is folk art fever dream territory. The main totem pole stands 90 feet tall, made from concrete and painted with bright, cartoonish symbols. The surrounding poles are just as detailed.
There’s no charge to walk the grounds, and a small on-site museum shows off Galloway’s woodworking and violin collection. No shade here, so bring water and visit early or late to avoid the Oklahoma heat.
Tulsa, Oklahoma
Oil rigs and trains—Tulsa’s Route 66 Historical Village brings both together. The restored Frisco 4500 locomotive is massive and perfect for photos. You’ll also see a replica 1920s gas station and the city’s tallest oil derrick.
There’s usually plenty of parking and it’s self-guided, so stay as long (or short) as you want. Good stop for kids who like big machines. Plus, it’s free.
Amarillo, Texas
Cadillac Ranch is chaos in the best way. Ten Cadillacs buried nose-first in the dirt, and you’re supposed to spray paint them. Yep, BYO spray paint (or buy some from the pop-up sellers nearby).
The cars are always changing, layered in graffiti. It’s messy, fun, and weirdly satisfying. Parking is along the access road. Look for the gate and follow the dirt path.
Winslow, Arizona
You really do stand on a corner in Winslow, Arizona—Eagles fans know the line. The park has a bronze statue, a mural with a flatbed Ford, and speakers looping the song. Nearby gift shops lean heavy into classic rock, but it’s part of the charm.
Street parking is free. For food, try RelicRoad Brewing Company just across the street. Great burgers and a perfect view of the corner.
Holbrook, Arizona
The Wigwam Motel lets you sleep in concrete teepees surrounded by vintage cars. The rooms are basic but clean. Expect a small bathroom, a firm bed, and major retro vibes.
Each wigwam has its own driveway, so parking is easy. Rates run about $100–$120 a night. Book early, especially in summer. If you’re hungry, Joe & Aggie’s Café down the road serves solid New Mexican comfort food.
