Route 66: The All-American Road Trip Dream

6 November 2025

If you've ever dreamed of hitting the open road with the radio turned up, wind in your hair, and not a care in the world, Route 66 is the perfect adventure for you. This legendary highway, often called the "Main Street of America," embodies the heart and soul of the great American road trip.

Spanning eight states from Chicago to Santa Monica, Route 66 is more than just a highway—it's a time machine that takes you through decades of American history, culture, and quirky roadside attractions. Buckle up because we're about to take a virtual cruise down the most iconic road in the U.S.!

A Brief History of Route 66

Route 66 was officially established in 1926, connecting small towns, big cities, and everything in between. During the Dust Bowl era in the 1930s, thousands of families used this road to migrate to the West, seeking better lives. The highway became a symbol of hope, freedom, and opportunity.

As America embraced the automobile culture in the 1950s, Route 66 flourished. Motels, diners, and roadside attractions popped up, offering weary travelers a place to rest and refuel. Unfortunately, with the expansion of the Interstate Highway System in the 1980s, Route 66 was decommissioned, causing many of its businesses to fade into history.

But the spirit of Route 66 never died. Thanks to passionate preservationists and road trip lovers, the historic highway remains alive and well, inviting adventurers to relive its golden days.

Planning Your Route 66 Road Trip

Before you throw your suitcase in the trunk and hit the road, a little planning goes a long way. A full Route 66 trip covers over 2,400 miles, so you'll want to map out your must-see spots, book accommodations, and prepare for some long drives.

Best Time to Travel

Route 66 can be traveled year-round, but the best time is spring (April - June) and fall (September - October) when temperatures are mild and the scenery is stunning. Summer is popular but can be scorching, especially in Arizona and New Mexico, while winter might bring snow in the Midwest.

How Long Does It Take?

If you want to do Route 66 justice, aim for two to three weeks. Of course, if you're short on time, you can always do specific sections instead of the full stretch.

What to Pack

- Comfortable Clothes & Shoes – You'll be walking around towns and attractions, so dress comfortably.
- Sunscreen & Sunglasses – The sun can be relentless, especially in the Southwest.
- Camera or Smartphone – You'll want to capture every unique roadside stop!
- Maps & Apps – Google Maps is great, but a physical Route 66 guidebook adds to the nostalgia.
- Emergency Kit – Flat tires and unexpected car troubles can happen on the road.

Must-See Attractions Along Route 66

From neon-lit motels to bizarre roadside oddities, Route 66 is packed with unforgettable sights.

1. Chicago, Illinois – The Official Starting Point

Your journey begins in the Windy City. While in Chicago, don’t forget to grab a deep-dish pizza before taking a picture at the Route 66 starting sign.

2. The Gemini Giant – Wilmington, Illinois

This towering fiberglass spaceman is one of the quirkiest roadside stops. A remnant of mid-century advertising, it's a great spot for a photo op.

3. Gateway Arch – St. Louis, Missouri

While technically not on Route 66, the Gateway Arch is close enough and symbolizes the westward expansion of America. Take a tram ride to the top for breathtaking views.

4. Meramec Caverns – Stanton, Missouri

These limestone caves claim to have once been a hideout for the outlaw Jesse James. Whether or not that's true, the underground formations are mesmerizing.

5. Blue Whale of Catoosa – Catoosa, Oklahoma

One of the most beloved Route 66 roadside attractions, this giant smiling whale sculpture has been delighting travelers since the 1970s.

6. Cadillac Ranch – Amarillo, Texas

A row of old Cadillacs buried nose-first in the ground, Cadillac Ranch invites visitors to add their own graffiti art to these rusting relics.

7. Petrified Forest National Park – Arizona

This park is home to ancient petrified wood and vibrant badlands. It's a surreal contrast to the neon signs and diners you'd typically associate with Route 66.

8. Wigwam Motel – Holbrook, Arizona

Ever wanted to sleep in a teepee? This vintage motel offers a quirky overnight stay in concrete wigwams, reminiscent of the mid-century golden age of travel.

9. Santa Monica Pier – California – The End of Route 66

Your journey ends at the iconic Santa Monica Pier, where you can celebrate with a sunset over the Pacific Ocean. The “End of the Trail” sign marks the completion of your epic road trip.

The Route 66 Food Experience

A road trip isn’t complete without indulging in some classic roadside eats. Lucky for you, Route 66 is packed with legendary diners and eateries.

Lou Mitchell’s – Chicago, Illinois

Famous for its massive breakfasts, this diner has been around since the 1920s. Start your journey with a plate of fluffy pancakes or a hearty omelet.

The Big Texan Steak Ranch – Amarillo, Texas

Think you can finish a 72-ounce steak in under an hour? If so, it's free! This famous challenge has attracted hungry travelers for decades.

Delgadillo’s Snow Cap – Seligman, Arizona

This wacky drive-in is known for its offbeat humor and delicious burgers. The friendly staff might play a few pranks on you, but it's all in good fun.

Why Route 66 Is Still a Must-Do Today

You might be wondering, “Is Route 66 still worth the hype?” Absolutely! There’s nothing quite like the feeling of driving down this historic road, surrounded by open landscapes, neon-lit motels, and slices of pure Americana.

Unlike modern highways that focus on efficiency, Route 66 is about the journey, not just the destination. It’s about pulling over for a bizarre roadside attraction, chatting with friendly locals at a small-town diner, and embracing the beauty of slowing down.

Final Thoughts

Route 66 isn’t just a road—it’s a connection to America's past, a bridge between generations, and a symbol of freedom. Whether you're a history buff, a nostalgic traveler, or just someone looking for an unforgettable adventure, this legendary highway won't disappoint.

So, what are you waiting for? Pack your bags, fuel up the car, and hit the road. Because Route 66 is more than just a drive—it’s a dream.