There’s a reason Route 66 is called The Mother Road. Stretching nearly 2,500 miles from Chicago, Illinois to Santa Monica, California, this legendary highway captures the heart of America’s road trip culture. Driving Route 66 isn’t just about covering miles — it’s about slowing down, exploring quirky roadside attractions, and experiencing small-town America. If you’re planning a road trip along Route 66, you’ll want to know the best Route 66 attractions from Chicago to Santa Monica that make this historic highway unforgettable.
Starting Point: Route 66 in Chicago, Illinois
Route 66 officially begins at Adams Street in downtown Chicago. Before you head west, take a photo at the “Begin Route 66” sign, and then fuel up with a Chicago-style deep-dish pizza. Don’t miss the Route 66 Welcome Center at the Chicago Cultural Center, where you can pick up maps and learn a bit about the road’s history.
Must-See Attractions in Illinois
-
Gemini Giant in Wilmington – A towering Muffler Man statue holding a rocket, one of the most iconic Route 66 photo stops.
-
Pontiac’s Route 66 Hall of Fame & Museum – Packed with vintage cars, memorabilia, and murals celebrating the road’s golden era.
-
Cozy Dog Drive-In, Springfield – Birthplace of the original corn dog, a must-try roadside snack.
Route 66 Through Missouri
Missouri offers a mix of historic towns and scenic landscapes. In St. Louis, drive across the Chain of Rocks Bridge, a mile-long historic bridge over the Mississippi River.
Top Missouri Stops
-
Meramec Caverns in Stanton – A famous cave system once rumored to be Jesse James’ hideout.
-
Route 66 State Park – Great for a quick stop with trails, a museum, and vintage gas station exhibits.
-
Gay Parita Sinclair Station in Paris Springs – A lovingly restored 1930s gas station, perfect for photos.
Route 66 in Kansas: The Shortest Stretch
Kansas has only 13 miles of Route 66, but it’s packed with charm.
-
Cars on the Route, Galena – A restored Kan-O-Tex gas station with “Tow Tater,” the truck that inspired Mater from Cars.
-
Rainbow Bridge – A historic concrete arch bridge, one of the last of its kind.
Oklahoma: Heart of Route 66
Oklahoma has the longest stretch of Route 66, with over 400 miles of road dotted with neon signs and vintage diners.
Oklahoma Highlights
-
Blue Whale of Catoosa – A quirky roadside giant whale sculpture built in the 1970s, now a beloved landmark.
-
Pops 66 Soda Ranch in Arcadia – Famous for its giant soda bottle and selection of hundreds of soda flavors.
-
Oklahoma Route 66 Museum, Clinton – Tells the story of the road’s cultural impact through interactive exhibits.
Texas Panhandle: Big Skies and Bigger Stops
Crossing into Texas, Route 66 shrinks to about 150 miles, but the wide-open landscapes make for incredible driving.
Texas Attractions
-
Cadillac Ranch, Amarillo – Spray-paint your mark on 10 half-buried Cadillacs in the desert.
-
Big Texan Steak Ranch – Try the legendary 72-ounce steak challenge, a Route 66 tradition.
-
U-Drop Inn, Shamrock – An Art Deco gas station and café that’s one of the best-preserved Route 66 landmarks.
New Mexico: Culture and Color
In New Mexico, Route 66 follows both the old and newer alignments, taking you through Albuquerque, Santa Fe, and Gallup.
New Mexico Must-Sees
-
Santa Fe Plaza – Explore Native American markets, adobe architecture, and Route 66 history.
-
66 Diner, Albuquerque – Retro vibes with milkshakes and neon lights.
-
El Rancho Hotel, Gallup – Once home to Hollywood stars filming Westerns, this historic hotel is dripping with charm.
Arizona: Desert Beauty and Classic Stops
Arizona boasts some of the most scenic stretches of Route 66, including the longest remaining continuous stretch of the original road.
Arizona Attractions
-
Petrified Forest National Park – Drive through landscapes filled with ancient fossilized wood.
-
Winslow, Arizona – “Standin’ on the Corner” park, made famous by the Eagles song.
-
Meteor Crater – A massive impact site that’s both eerie and fascinating.
-
Seligman – Known as the birthplace of Route 66 revival, with kitschy shops and diners.
-
Hackberry General Store – A vintage gas station turned museum and photo spot.
California: Final Stretch to Santa Monica
California is the final leg of the journey, where Route 66 passes through desert towns, the San Bernardino Mountains, and into Los Angeles.
California Highlights
-
Elmer’s Bottle Tree Ranch – A forest of bottle trees made from glass bottles and scrap metal.
-
Wigwam Motel, San Bernardino – Stay in a teepee-shaped motel, a classic Route 66 experience.
-
Santa Monica Pier – The official end of Route 66, where you can stand by the “End of the Trail” sign and take in Pacific Ocean views.
Why Drive Route 66 Today?
Driving Route 66 from Chicago to Santa Monica is not just a road trip; it’s a nostalgic journey into America’s past. Each stop — whether it’s a neon diner, a quirky roadside attraction, or a stunning desert view — tells the story of how Americans once traveled before interstates bypassed small towns. It’s about history, culture, and adventure rolled into one.
FAQs About Route 66 Attractions
Q: How long does it take to drive Route 66 from Chicago to Santa Monica?
Most travelers take two to three weeks to explore Route 66 attractions fully. Driving nonstop would take about a week, but the beauty of Route 66 is in the stops along the way.
Q: What are the most famous Route 66 attractions?
Some of the most iconic attractions include the Cadillac Ranch in Texas, the Blue Whale of Catoosa in Oklahoma, the Wigwam Motel in California, and the Santa Monica Pier at the end of the road.
Q: Is Route 66 still drivable?
Yes, though parts of the original road have been replaced by highways, most of the route remains accessible. Many towns and businesses along Route 66 have preserved their landmarks for travelers.
Q: What’s the best time of year to drive Route 66?
Spring and fall are ideal, as summers can be very hot in the Southwest, while winters bring snow in the Midwest.
Q: Can you do Route 66 in an RV?
Absolutely! Many RV travelers enjoy Route 66 because of the numerous campgrounds and RV parks along the way.
Final Thoughts
From Chicago’s skyscrapers to Santa Monica’s ocean breeze, Route 66 is the ultimate American road trip. Each stop tells a story — whether it’s a roadside diner, a neon-lit motel, or a breathtaking desert view. By visiting Route 66 attractions from Illinois to California, you’re not just taking a trip, you’re stepping into living history.
So pack your bags, fill up the tank, and get ready to chase the spirit of adventure along Route 66.