1. “Begin 66” Sign — Chicago, Illinois
Snap the obligatory selfie at East Adams & Michigan Avenue, then carb-load on deep-dish before the odometer starts rolling.
Choose Chicago visitor map
2. The Gemini Giant — Wilmington, Illinois
Space helmet? Check. Rocket? Check. The 28-foot mascot guards the Launching Pad Drive-In—still slinging burgers under lunar-green neon.
Official Launching Pad site
3. Old Chain of Rocks Bridge — St. Louis, Missouri
A mile-long pedestrian span that kinks 22° mid-river. Park, walk the bend and watch the Mississippi churn under rusty trusses.
Great Rivers Greenway info
4. Meramec Caverns Barn Sign — Stanton, Missouri
Jesse James never hid here, but thousands of barn roofs swear otherwise. Tour the kitschy cave, then grab salt-water taffy at the gift shop as big as a gymnasium.
Meramec Caverns official
5. Blue Whale — Catoosa, Oklahoma
Built as an anniversary gift (flowers are overrated), the 80-foot cement cetacean now hosts selfie pilgrims and the occasional turtle.
Travel OK listing
6. Cadillac Ranch — Amarillo, Texas
Ten tail-finned Caddies nose-planted in a wheat field. Bring a spray can; your art lasts three hours before the next road-tripper paints over it.
Visit Amarillo page
7. Midpoint Café — Adrian, Texas
Concrete marker reads “1 139 miles to L.A. / Chicago.” Celebrate halftime with a slab of Ugly-Crust pie smothered in ice cream.
Midpoint Café website
8. Blue Swallow Motel — Tucumcari, New Mexico
Rose-pink stucco, garage bays for each room and a neon swallow glowing electric-blue since 1939. Ask for Room 4—rumoured cameo in Cars.
Blue Swallow Motel
9. Route 66 Auto Museum — Santa Rosa, New Mexico
Fins, whitewalls and fuzzy dice: 30-plus lovingly restored classics and a jukebox that eats quarters faster than a Vegas slot.
Museum site
10. Petrified Forest & Painted Desert — Arizona
The only national park on Route 66. Ancient log “gems” glitter under desert sun; a rusty Studebaker marks the original roadbed.
NPS park page
11. Wigwam Motel — Holbrook, Arizona
“Have You Slept in a Wigwam Lately?” Fifteen concrete teepees circle vintage Chevys—sleeping inside feels weirdly cozy (and smells faintly of cedar).
Wigwam Motel reservations
12. “Standin’ on the Corner” Park — Winslow, Arizona
Eagles fans queue for the bronze troubadour and flatbed-Ford mural. Speakers loop “Take It Easy”; good luck getting it out of your head before California.
Official corner foundation
13. Meteor Crater — Winslow, Arizona
A mile-wide, 560-foot-deep dent blasted 50 000 years ago. The visitor centre’s chunk of space rock is selfie-heavy and security-guarded.
Meteor Crater visitor info
14. Wild Burros of Oatman, Arizona
Former mining town now owned by free-range burros descended from pack animals. Carrots from the general store will win furry friends—watch the nibbles.
Visit Arizona: Oatman
15. “End of the Trail” Sign — Santa Monica Pier, California
Roll past roller-coasters and the Pacific stretch. Grab a corn dog, toast the sunset—odometer reads “done.”
Santa Monica Pier guide
So, how many did you tick off? 1 – 5 = rookie, 6 – 10 = road warrior, 11 – 15 = certified Mother Road legend. Drop your score (and any secret detours) below.
Related reads on travelleri.com:
• Hungry en route? Try 12 Street-Food Dishes Worth Flying For.
• Chase short hikes between the stops with 10 Epic Hikes You Can Finish Before Lunch.