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TABLE OF CONTENTS

• Route 66 100th Anniversary 2026
• ROUTE 66: CHICAGO TO SANTA MONICA
• THE CLASSIC BIKER ROUTE 66 ROUTE (CHICAGO TO SANTA MONICA)
• THE ROUTE 66 CENTENNIAL IN 2026 IS A BIG DEAL
• ROUTE 66 ROAD TRIP PLANNING GUIDE
• EXPLORE ROUTE 66 IN 2026: GUIDED TOUR OPTIONS & PACKAGES
• ROUTE 66 CENTENNIAL EVENTS
• HOW TO DRIVE ROUTE 66 IN 2026
• ROUTE 66 ITINERARY CHICAGO TO SANTA MONICA
• BEST STOPS ON HISTORIC ROUTE 66 FOR 2026
• ROUTE 66 ROAD TRIP PLANNING GUIDE FOR 2026
• ROUTE 66 TRAVEL TIPS
• ROUTE 66 100TH ANNIVERSARY 2026 ROAD TRIP PLAYLIST
• ROUTE 66 END OF THE TRAIL

ROUTE 66: CHICAGO TO SANTA MONICA

Route 66 is known as ‘The Mother Road’ because it linked the Midwest to the Pacific and runs roughly 2,448 miles across eight states – from Illinois to Missouri to Kansas to Oklahoma to Texas to New Mexico to Arizona to California.

The nickname ‘The Mother Road’ first came from The Grapes of Wrath (1939) by John Steinbeck. In the novel, Steinbeck refers to Route 66 as ‘the mother road, the road of flight’ as it became a lifeline for families escaping the Dust Bowl during the Great Depression.

Route 66 was actually decommissioned in 1985 but it never disappeared. It goes on living on through its historic alignments, the hand-painted signs, the neon-lit motels, and the communities that refuse to let the road fade away.

THE CLASSIC BIKER ROUTE 66 ROUTE (CHICAGO TO SANTA MONICA)

My best friend Dina recently did ‘an Easy Rider‘ for real and rode a Harley Davidson motorcycle along the entire route from Chicago and across America to the famous pier at Santa Monica California, where there is a legendary ‘end of Route 66 sign’.

She said the trip was both exhilarating and exhausting as it was done in just ten days, but what she loved most was that every state felt so different, because one day you’re rolling past brick main streets and cornfields and the next you’re cruising through desert landscapes that felt straight out of a movie.

She told me that in Illinois & Missouri it’s all about the classic beginnings, historic downtowns, and that big first-day anticipation and raw energy. Then through Oklahoma it’s the experience of long stretches of preserved Route 66 and some of the best museums before reaching the Texas Panhandle with its huge skies, roadside art, and Amarillo legends.

In New Mexico there’s neon signs, the turquoise skies, and the unforgettable sunsets. And Arizona is about the red rocks, trading posts, and jaw-dropping scenery before finally and exhilaratingly reaching California, with its vast areas of open desert before finally detecting the scent of the Pacific Ocean on the breeze, and that promised iconic end-of-the-road moment.

THE ROUTE 66 CENTENNIAL IN 2026 IS A BIG DEAL

Turning 100 isn’t just symbolic. Communities along Route 66 have been preparing for this centenary year for years and 2026 will be filled with festivals, exhibits, car cruises, and local celebrations that bring the road’s history to life. It’s a rolling celebration across the entire route, town by town.

ROUTE 66 ROAD TRIP PLANNING GUIDE

HOW TO DRIVE ROUTE 66 IN 2026

ROUTE 66 ITINERARY CHICAGO TO SANTA MONICA

BEST STOPS ON HISTORIC ROUTE 66 FOR 2026

1. Chicago, Illinois – The Official Starting Point: Begin your Route 66 adventure in Chicago, where the Mother Road originally kicked off toward the west. Enjoy classic eats, museums, and city culture before you hit the open road. Check accomodation availability in Downtown Chicago.

2. Chain of Rocks Bridge (Missouri/Illinois): A historic engineering marvel over the Mississippi River. This dramatically curved bridge is a classic photo stop and a reminder of the road’s early days. Check accomodation availability.

3. Gemini Giant & Retro Roadside Icons (Illinois): Iconic neon and fiberglass giants — especially the Gemini Giant — capture that classic Route 66 roadside aesthetic. These quirky stops make for fun photos and storytelling. Check accomodation.

4. Blue Whale of Catoosa (Oklahoma): One of Route 66’s most beloved oddball landmarks — the 80-foot-long Blue Whale is a lovable detour and a must-see for nostalgic road trippers. Check accomodation availability.

5. Midpoint Café (Adrian, Texas): Stop at the famed Midpoint Café, marking the halfway point of the Route 66 journey. It’s a classic photo-op and a great place to take a breather and share stories with fellow travellers. Check accomodation.

6. Cadillac Ranch (Amarillo, Texas): This playful public art installation of half-buried Cadillacs is one of Route 66’s most photographed roadside attractions and, in 2026, it will be buzzing with centenary visitors. Check accomodation availability.

7. Standin’ on the Corner Park (Winslow, Arizona): Famous from the Eagles’ song Take It Easy, this small park is a cultural landmark for music lovers and classic road trippers alike. Check accomodation availability.

8. Blue Swallow Motel (Tucumcari, New Mexico): An iconic neon-lit stay that evokes the romance of historic Route 66 lodging and is perfect for photography, overnight rest, and nostalgia. Check accomodation availability.

9. The Painted Desert and Petrified Forest (Arizona): Though slightly off the original alignment, these stunning natural landscapes are often paired with Route 66 itineraries and offer awe-inspiring scenery that contrasts beautifully with roadside kitsch. Check accomodation availability.

10. Kingman, Arizona – Route 66 Museums & Centennial Events: Kingman serves as a hub for centennial events (like bike weeks, historic parades, and car shows), and it’s home to Route 66 museums that delve into local and national history. Check accomodation availability.

11. Oatman, Arizona – Wild West Authenticity: A quirky former mining town where burros roam freely down the main strip, Oatman offers a living slice of frontier atmosphere perfect for unique moments along the drive. Check accommodations.

12. Santa Monica Pier, California – “End of the Trail”: No Route 66 road trip is complete without arriving at the iconic sign on Santa Monica Pier — the official western terminus and perfect photo finish for your centenary celebration. Check accommodations and availability in Santa Monica.

ROUTE 66 ROAD TRIP PLANNING GUIDE FOR 2026

ROUTE 66 TRAVEL TIPS

1. Collect The Stamps: The US Postal Service is celebrating Route 66 Centenary with a collection of postage stamps depicting scenes from the historic route.

2. Anchor your trip around a mix of big attractions and authentic local stops as that’s often where unforgettable moments can happen. Watch local calendars as many small-town centennial events are announced closer to the date.

3. Book early especially in iconic towns as 2026 will be busy. Classic motels and popular stops will fill fast. If you have your heart set on neon, reserve as far in advance as you possibly can.

4. Don’t expect one continuous “Route 66 road” as the Route 66 of today is a patchwork of historic alignments, frontage roads, and modern highways. Use a Route 66 specific map or app use offline navigation as cell service can vanish fast.

5. Best Time to Drive Route 66 is Springtime (April–May) for cooler deserts and wildflowers. In the Fall (September–October) for ideal temps and golden light. Summer is doable but desert heat is no joke so plan early-morning drives.

6. Build your trip around ‘anchor towns’ and a mix of big attractions and authentic local stops as that’s often where unforgettable moments can happen. Instead of obsessing over every mile, choose key overnight stops, then explore what’s in between to keep your trip relaxed and flexible.

7. Prep your vehicle for the journey. Check tires (if driving a car – including the spare). Carry water, sunscreen, and chargers. Fill up on fuel before long rural stretches.

8. Spend local to support small businesses. Every diner meal, motel night, and museum ticket helps keep Route 66 alive. Supporting small businesses is part of the experience.

9. How long does it take to drive Route 66? Could you rush it in a week? Technically, yes. Would I recommend that? Absolutely not. The ideal recommendation for 2026 is to take ten to fourteen days as a minimum. This gives you time to take a detour without stressing over your itinerary. To attend centennial events and talk to locals (some of the best moments happen in diners) and to actually enjoy the road instead of chasing time and mileage.

10. Remember that the most memorable Route 66 moments are often unplanned. Building flexibility into your schedule gives you the freedom to say yes when the road offers something unexpected and during the 100th anniversary those moments will be everywhere.

ROUTE 66 100TH ANNIVERSARY 2026 ROAD TRIP PLAYLIST

This is my own hand-picked Route 66 in 2026 road trip playlist – with classic hits and iconic Americana tracks designed to play in sync with the road and that will capture the spirit of the journey from Chicago to Santa Monica and to make sure you get your kicks on Route 66!

ROUTE 66 END OF THE TRAIL

And if you’re anything like me, that anticipated moment when you reach the ‘End of the Trail’ sign at the Santa Monica Pier will feel less like the end of a road trip and more like the beginning of a lifelong obsession with the Mother Road.

On Route 66 in 2026, you won’t just be driving through history.
You’ll be driving through a living breathing celebration of it!

Are you planning a Route 66 trip?

In 2026 or any other time?

Have you already experienced Route 66?

Let me know – I’d love to read your comment!