Travel Itinerary
Route 66 stretches across eight states from Chicago to Santa Monica, covering over 2,400 miles of American history.
This legendary highway opened in 1926 and became the main path for families heading west during tough times.
Today, millions of travelers still cruise this famous road to experience classic diners, quirky roadside attractions, and small-town charm that captures the spirit of adventure.
1. Beginning Of Route 66 Sign In Chicago
Every epic journey needs a starting point, and Chicago’s iconic Route 66 sign marks the official beginning of America’s most famous highway.
Located at the intersection of Adams Street and Michigan Avenue, this simple brown sign attracts thousands of visitors yearly who want to snap photos before their cross-country adventure.
Standing here feels like stepping back in time to when families packed their cars for new opportunities out west.
2. Chain Of Rocks Bridge
This mile-long bridge connecting Illinois and Missouri features a weird 22-degree bend that makes driving across it feel like a roller coaster ride.
Built in 1929, the bridge served Route 66 travelers for decades before closing to cars in 1970.
Now pedestrians and cyclists can walk across this engineering marvel while enjoying stunning views of the Mississippi River below and feeling the history beneath their feet.
3. Galaxy Giant In Wilmington Illinois
Standing 28 feet tall, this fiberglass spaceman has been welcoming visitors to Wilmington since 1965, making him older than many grandparents.
Originally called the Muffler Man, locals renamed him the Galaxy Giant because of his space-age appearance and cosmic green color.
Kids love posing next to this friendly giant who represents the quirky roadside attractions that made Route 66 famous nationwide.
4. Old Riverton Store In Kansas
This tiny store proves that good things come in small packages, serving travelers since 1925 with cold drinks and friendly conversation.
Owner Scott Nelson keeps the place running exactly like it was decades ago, complete with vintage gas pumps and old-fashioned hospitality.
Stepping inside feels like visiting your great-grandparents’ general store, where everyone knows your name and stories flow as freely as the soda pop.
5. Blue Whale Of Catoosa Oklahoma
Hugh Davis built this 80-foot concrete whale in the 1970s as a swimming hole for his family, never imagining it would become Oklahoma’s most photographed attraction.
The whale sits in a small pond where kids once dove off its tail and slid down its sides during hot summer days.
Though swimming ended years ago, families still climb aboard this gentle giant for pictures and picnics in the surrounding park.
6. Ed Galloway’s Totem Pole Park Oklahoma
Ed Galloway spent 11 years carving the world’s largest concrete totem pole, reaching 90 feet into the Oklahoma sky like a colorful skyscraper.
This folk art teacher created over 300 totem poles throughout the park using only hand tools and incredible patience.
Visitors can climb inside the main totem pole and peek out windows while learning about Native American culture and one man’s artistic vision come to life.
7. Cadillac Ranch Amarillo Texas
Ten Cadillacs buried nose-first in a Texas wheat field create one of America’s weirdest and most wonderful art installations.
Artists Chip Lord, Hudson Marquez, and Doug Michels planted these cars in 1974 to represent the evolution of Cadillac tail fins through the years.
Visitors bring spray paint cans to add their own artwork to these colorful cars, making Cadillac Ranch a constantly changing masterpiece of public creativity.
8. Devil’s Rope Museum McLean Texas
Barbed wire might sound boring, but this museum makes fence-building fascinating with displays showing how sharp wire changed the American West forever.
The museum houses over 2,000 varieties of barbed wire, proving that even the simplest inventions can have complex histories.
Kids discover how cowboys, farmers, and ranchers used different wire patterns while adults appreciate the craftsmanship behind these twisted metal barriers that tamed the frontier.
9. Texas Route 66 Museum McLean Texas
McLean hits the jackpot with two fantastic museums on the same street, making this tiny town a major stop for history buffs.
The Route 66 Museum showcases classic cars, vintage signs, and memorabilia from the highway’s golden age when families drove cross-country for adventure.
Interactive exhibits let visitors experience what travel was like before interstate highways, when every mile brought new discoveries and every small town offered unique treasures.
10. Leaning Tower Of Texas Groom Texas
This water tower leans at a crazy angle that makes visitors wonder if they need glasses or if gravity stopped working in Groom.
Actually a clever advertising trick for a truck stop, the tower was intentionally built to tilt dramatically, creating one of Route 66’s most photographed optical illusions.
Families stop to take silly pictures pretending to push the tower over or hold it up, creating memories that last long after the road trip ends.
11. U Drop Inn Shamrock Texas
This Art Deco masterpiece looks like something from a science fiction movie, with its gleaming tower and geometric shapes reaching toward the Texas sky.
Built in 1936, the U-Drop Inn served as both a gas station and restaurant, feeding hungry travelers with hearty meals and friendly service.
Now restored to its original glory, this architectural gem proves that even gas stations can be beautiful when designed with creativity and pride in craftsmanship.
12. Petrified Forest National Park Arizona
Millions of years ago, giant trees fell and turned to colorful stone, creating a rainbow forest where wood became precious gems.
The park protects thousands of petrified logs scattered across painted desert landscapes that look like an alien planet from outer space.
Hikers can walk among these ancient tree fossils while learning how time and minerals transformed living wood into beautiful stone sculptures that sparkle in the Arizona sunshine.
13. Wigwam Motel Holbrook Arizona
Sleep inside a concrete teepee at this unique motel where each room is shaped like a Native American dwelling from the 1950s.
The Wigwam Motel represents classic roadside architecture when motels competed for attention with creative designs instead of boring rectangular buildings.
Families love staying in these cozy wigwams that offer modern comfort inside traditional shapes, creating a camping experience without leaving civilization behind for the wilderness.
14. Delgadillo’s Snow Cap Drive In Seligman Arizona
Juan Delgadillo opened this wacky drive-in in 1953 and filled it with enough jokes, puns, and silly signs to make everyone laugh.
The menu offers items like “dead chicken” and “cheeseburgers without cheese,” while fake mustard bottles squirt yellow string instead of condiment.
Three generations of the Delgadillo family continue serving great food with even better humor, proving that laughter really is the best seasoning for any meal.
15. Elmer’s Bottle Tree Ranch Oro Grande California
Elmer Long planted a forest of metal trees decorated with thousands of colorful glass bottles that catch sunlight and create rainbow sparkles.
Each bottle tree stands like a sculpture garden where recycling becomes art and trash transforms into treasure through creative vision.
Visitors walk among these glittering trees while learning how one man’s hobby grew into a roadside attraction that brings joy to travelers from around the world.
16. Roy’s Motel And Café Amboy California
Roy’s sits in the middle of nowhere like a mirage in the Mojave Desert, serving travelers since 1938 with gas, food, and hope.
This remote outpost became famous when the National Trails Highway brought steady traffic through the harsh desert landscape.
Today, Roy’s stands as a symbol of survival and determination, showing how small businesses kept America’s highways running during the golden age of automobile travel.
17. Aztec Hotel Monrovia California
This Mayan-inspired hotel looks like an ancient temple dropped into suburban California, complete with colorful murals and mysterious stone carvings.
Built in 1925, the Aztec Hotel attracted Hollywood stars and wealthy travelers who wanted luxury accommodations with exotic architectural flair.
The hotel’s restaurant and bar continue serving guests under painted ceilings that tell stories of ancient civilizations while providing modern comfort and excellent cuisine.
18. Bagdad Café Newberry Springs California
This desert diner became world-famous after appearing in a German movie about friendship, dreams, and the magic of small-town America.
The original Bagdad Cafe burned down, but a new version keeps the legend alive with international visitors seeking movie locations.
Travelers from Germany, Japan, and other countries make special trips to eat pie where the film was shot, proving that good stories can make any place special.
19. Route 66 End Santa Monica Pier California
After 2,400 miles of adventure, Route 66 ends at Santa Monica Pier where the Pacific Ocean meets the famous highway’s final mile.
The official End of Trail sign stands near the beach where families celebrate completing their cross-country journey with carnival rides and cotton candy.
Watching the sunset over the Pacific Ocean from this historic pier feels like the perfect ending to America’s greatest road trip adventure story.
20. Painted Desert Community Complex Arizona
Mary Colter designed this pueblo-style visitor center to blend perfectly with the colorful desert landscape using local stone and traditional Native American architecture.
The complex serves as headquarters for exploring the Painted Desert’s rainbow-colored hills that change colors throughout the day.
Visitors can learn about desert ecology, Native American history, and geology while enjoying panoramic views of one of America’s most beautiful and otherworldly natural landscapes.