Route 66 Turns 100: A Century of America’s Most Iconic Road Trip

Why Route 66 Is Still the Ultimate American Road Trip

Route 66 is not about speed. It is about discovery.

The route crosses eight states and links together small towns, roadside attractions, classic diners, and landscapes that feel endlessly cinematic. Even though Route 66 was officially decommissioned, large portions of the original road remain drivable today. Travelers keep returning because no other U.S. road trip offers the same mix of nostalgia, spontaneity, and character.

When I was 19, my best friend and I drove from Chicago to the Grand Canyon, following Route 66 for as long as we could. We stopped constantly, sometimes for famous landmarks and sometimes simply because something caught our eye. Twenty years later, I still consider it one of the trips of a lifetime. That’s what this road does. It lingers.

The Can’t-Miss Route 66 Stops

Route 66 is not the kind of road trip you rush through. It is the kind you build around moments. Along its nearly 2,500 miles, the highway stitches together legendary cities, tiny towns, bizarre roadside attractions, neon-lit motels, and landscapes that feel almost unreal. Some stops are famous, some are quietly magical, and some only make sense once you see them in person. If you are driving Route 66 for the first time, these are the places that capture the spirit of the Mother Road and prove why it still feels so unforgettable, a century later.

Chicago, Illinois: The Official Starting Point

• Begin Route 66 Sign on Adams Street

• Grant Park and surrounding downtown streets tied to Route 66 history

Chicago is where most Route 66 road trips begin, even if you only drive part of the route. The city offers a mix of historic signage, architecture, and classic photo ops that set the tone for the journey ahead.

Wilmington & Pontiac, Illinois: Classic Roadside Americana

• Gemini Giant, one of the most photographed Route 66 roadside statues

• Pontiac’s downtown murals and Route 66 landmarks

These Illinois stops introduce travelers to the playful, nostalgic spirit Route 66 is famous for. Giant statues, colorful murals, and small-town charm make this stretch feel like stepping into a living postcard.

St. Louis Area, Missouri: Murals, Diners, and Historic Crossings

• Historic Route 66 crossings near St. Louis

• Small towns with brick buildings, diners, and hand-painted murals

Missouri delivers some of the most authentic Route 66 scenery, especially if you enjoy unscripted stops and backroad detours. It’s a favorite stretch for travelers who want classic Americana without heavy crowds.

Galena & Riverton, Kansas: Short Stretch, Big Impact

• Galena Main Street, which inspired Cars’ Radiator Springs

• Preserved Route 66 structures around Riverton

Kansas has the shortest stretch of Route 66, but it packs in a surprising amount of history and visual charm. This section is a must-stop for fans of both Route 66 history and pop culture.

Catoosa & Arcadia, Oklahoma: Roadside Icons

• Blue Whale of Catoosa, a top Route 66 photo stop

• Pops Arcadia, famous for its giant soda bottle and massive drink selection

Oklahoma is often cited as the most intact stretch of Route 66, with long continuous segments of the original road still drivable. It feels like Route 66 at full expression, blending kitsch, history, and open-road freedom.

Amarillo, Texas: Art in the Open Plains

• Cadillac Ranch, one of the most recognizable Route 66 attractions

• Long drives through wide-open Texas landscapes

Amarillo sits in the heart of the Texas Panhandle and is one of the most searched-for Route 66 stops online. The contrast between large-scale art and wide-open landscapes makes this stretch especially memorable.

Tucumcari, New Mexico: Neon Motels and Night Photography

• Blue Swallow Motel and nearby vintage motor lodges

• Neon signs, murals, and classic Route 66 streets

New Mexico consistently ranks as one of the most photogenic sections of Route 66, especially after dark. Tucumcari’s neon-lit motels have become icons of the Route 66 aesthetic.

Petrified Forest & Winslow, Arizona: Desert and Music History

• Petrified Forest National Park, the only national park Route 66 passes through

• Standin’ on the Corner Park, tied to the classic Eagles song

This section blends surreal natural scenery with cultural history. Winslow is forever tied to the Eagles lyric “standin’ on a corner in Winslow, Arizona,” from Take It Easy—one of my all-time favorite Eagles songs and a soundtrack staple for any Route 66 road trip.

Grand Canyon Detour: A Legendary Side Trip

• Easy access from Route 66

• One of the most popular detours for Route 66 travelers

While not directly on Route 66, the Grand Canyon is one of the most common and rewarding detours. For many travelers, this side trip is where the road trip becomes truly unforgettable.

California Desert to the Pacific: The Final Stretch

• Desert highways dotted with old signage and cafés

• Urban Route 66 alignments leading toward the coast

• Santa Monica Pier and the End of the Trail sign

The final stretch of Route 66 moves from desert solitude into the sprawl of Southern California. Reaching the Santa Monica Pier, with the Pacific Ocean ahead, provides a natural and emotional ending to one of America’s most iconic road trips.

How to Plan a Route 66 Road Trip

Planning a Route 66 road trip does not mean committing to a nonstop drive from Chicago to California. One of the best things about Route 66 is that it was never meant to be rushed.

You don't need to drive the entire route to have an unforgettable experience. Many travelers start with just a portion of Route 66 and return later to explore the rest. Breaking the route into manageable sections makes the trip more relaxed, more flexible, and far more enjoyable.

For a first Route 66 road trip, three to five states is the sweet spot. This gives you enough distance to feel the rhythm of the open road while still leaving time to explore small towns, roadside attractions, and unexpected detours. Popular first-time segments include Illinois to Missouri, Oklahoma to New Mexico, or Arizona to California.

One of the most important rules of Route 66 is to stop often and follow your curiosity. Some of the best moments happen at places you did not plan for: a faded sign pointing to an old café, a local museum run by volunteers, or a diner that looks like it has not changed in decades. Route 66 rewards curiosity more than tight schedules.

Finally, stay in at least one vintage motel or motor lodge along the way. Neon signs, roadside parking, and retro rooms are part of the Route 66 experience. These classic motels are not just places to sleep, they are living pieces of road trip history and often become some of travelers’ favorite memories of the journey.

Route 66 is less about reaching the end and more about how slowly you are willing to get there.

At 100 years old, Route 66 remains one of the most recognizable travel routes in the world. It continues to attract road trippers, photographers, families, and nostalgia seekers because it offers something increasingly rare: a journey defined by discovery rather than efficiency.

FAQ: Route 66

What is Route 66 famous for?

Route 66 is famous for classic diners, roadside attractions, neon motels, and its lasting influence on American road trip culture.

Where does Route 66 start and end?

Route 66 starts in Chicago and ends at the Santa Monica Pier.

How many states does Route 66 pass through?

Route 66 passes through eight states: Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California.

Why is Route 66 called the Mother Road?

Route 66 earned the nickname because it served as a primary westward route for families seeking opportunity. The term was popularized by John Steinbeck in The Grapes of Wrath and came to symbolize movement, hope, and starting over.

Can you still drive Route 66 today?

Yes. Many original sections remain drivable as historic byways, often combined with modern roads.

How long does it take to drive Route 66?

Most travelers spend 10 to 14 days driving the full route, while shorter regional trips are very common.

What is the best section of Route 66?

Arizona and New Mexico are frequently cited as favorites due to scenery, preserved landmarks, and proximity to major natural attractions.