Get Your Kicks in 2026: Planning the Ultimate Route 66 Road Trip for its 100th Anniversary

From Chicago to California, celebrate a century of America’s Mother Road with this must-do guide.

Route 66 turns 100 in 2026—a milestone that makes now the perfect time to plan the road trip of a lifetime. Stretching 2,448 miles (3,940 km) across eight states, Route 66 is a living museum of Americana, nostalgia, and offbeat charm. Whether you’re a first-timer or a repeat adventurer, this guide will help you make the most of your journey as the world prepares to celebrate a century of the Mother Road. Or at the very least, I’m writing this guide as part of my own preparations to experience this historic road trip firsthand. I am creating this guide for myself as I plan to embark on this historic trip.

A Brief History of Route 66

Commissioned in 1926, U.S. Route 66 was one of the original highways in the U.S. Highway System. Designed to connect the rural heartlands to major cities, it ran from Chicago, Illinois to Santa Monica, California, passing through Missouri, Kansas, Oklahoma, Texas, New Mexico, and Arizona along the way. Nicknamed “The Mother Road” by John Steinbeck in The Grapes of Wrath, Route 66 became a symbol of American freedom and movement, especially during the Dust Bowl migration and post-WWII prosperity. Although officially decommissioned in 1985 in favour of the Interstate Highway System, much of the old road still exists today as Historic Route 66.

What’s in a Number?

In the 1920s, as the U.S. government developed the national highway system, a numeric naming convention was introduced: even numbers for east–west routes and odd numbers for north–south. The Chicago–Los Angeles route was initially proposed as Route 60, but after some debate, Route 66 was selected instead. Cyrus Avery, the influential planner known as the “Father of Route 66,” championed the number because it was easy to remember, had a catchy ring, and looked balanced on signage. His instincts proved correct—Route 66 became one of the most iconic road names in American travel history.

State-by-State Highlights and Must-Do Stops

As you prepare for the centennial celebration of Route 66 in 2026, these curated stops across all eight states will help you experience the very best of what the Mother Road has to offer. From iconic roadside attractions and neon-lit diners to natural wonders and nostalgic small towns, each stretch of the journey offers a unique window into the American story—one that unfolds mile by mile along this historic route.

Here are the most iconic and unforgettable stops from east to west.

Illinois: Where It All Begins

Start in Chicago at the historic “Route 66 Begin” sign on Adams Street.
Lou Mitchell’s Restaurant (Chicago): A classic breakfast joint since 1923.
Gemini Giant (Wilmington): A towering Muffler Man statue holding a rocket.
Illinois Route 66 Hall of Fame (Pontiac): Murals, memorabilia, and history.

Missouri: Gateway to the West

Gateway Arch (St. Louis): Take the tram for sweeping views of the Mississippi River.
Ted Drewes Frozen Custard (St. Louis): Beloved for over 80 years.
Meramec Caverns (Stanton): Claimed to be a hideout of Jesse James.
Route 66 State Park (Eureka): Scenic trails and visitor exhibits.

Kansas: Smallest but Mighty

Cars on the Route (Galena): Inspiration for Tow Mater in Pixar’s Cars.
Rainbow Bridge (Riverton): A 1923 Marsh arch bridge.

Oklahoma: Route 66’s Beating Heart

Route 66 Museum (Clinton): Deep dive into history and culture.
Pops 66 Soda Ranch (Arcadia): Home to a 66-foot soda bottle and hundreds of soda flavours.
Blue Whale of Catoosa: A charming roadside photo op.
Tulsa & Oklahoma City: Known for Art Deco buildings and cultural museums.

Texas: Panhandle Quirks and Classics (1/2 Way There)

Cadillac Ranch (Amarillo): Graffiti-covered Cadillacs planted nose-down in a field.
Big Texan Steak Ranch (Amarillo): Try the 72-ounce steak challenge.
Midpoint Cafe (Adrian): Exactly halfway between Chicago and Santa Monica.
Historic 6th Street (Amarillo): Retro shops and neon lights.

New Mexico: Desert Charm and Native Heritage

Tucumcari: Neon-lit motels like the Blue Swallow offer vintage vibes.
Santa Fe Loop: An optional detour steeped in Pueblo architecture and art.
Albuquerque: Explore murals, diners, and ride the Sandia Peak Tramway.
Gallup: Gateway to Native American trading posts and art markets.

Arizona: Natural Wonders and Wild West Towns

Petrified Forest National Park: Colourful badlands and ancient fossils.
Winslow: “Standin’ on the Corner” made famous by The Eagles.
Meteor Crater: One of the world’s best-preserved impact sites.
Seligman: A kitschy slice of Route 66 life.
Grand Canyon: Detour-worthy and only 1.5 hours north from Williams.

California: From Desert to Ocean

Oatman: Historic mining town with wild burros roaming the streets.
Roy’s Motel & Café (Amboy): Iconic neon sign in the Mojave Desert.
Santa Monica Pier: Official end of Route 66, marked by the “End of the Trail” sign.

Collecting Route 66 Decals and Souvenirs

To mark your journey, travellers often collect Route 66 decals for their cars, RVs, or luggage. These come in:

State-specific Route 66 shield stickers
Full-route maps or milestone badges
Customisable “I Drove Route 66” labels

Look for them at visitor centres, museums, souvenir shops, or online marketplaces like Etsy and Amazon. Weatherproof and removable versions are great for vehicles.

Tips for Travelling Route 66 in 2026

Start Planning Early: 2026 will be a banner year with special centennial events.
Best Time to Travel: Spring and autumn offer the most pleasant driving weather.
Allow 2-3 weeks to enjoy the full route without rushing.
Use paper maps or Route 66-specific apps to navigate original alignments.
Stay in vintage motels and eat at mom-and-pop diners to embrace the true spirit of the road.
Collect decals from each state to commemorate your journey.

Why Route 66 Still Matters

More than just a highway, Route 66 is a journey through America’s cultural, economic, and emotional history. It tells stories of migration, reinvention, and resilience. In 2026, as travellers from around the world hit the road to celebrate its centennial, Route 66 offers a reminder to slow down, take the scenic route, and savour the soul of the journey.

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Every journey leaves a mark, and small choices can make a big difference. Choosing eco-friendly stays, supporting local communities, and being mindful of plastic use help preserve the beauty of the places we visit. Respecting wildlife, conserving resources, and travelling sustainably ensure future generations can experience the same wonders. By treading lightly and embracing responsible travel, we create meaningful connections and lasting memories. Here’s to adventures that inspire and footprints that honour our planet. Safe and mindful travels!

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