The Ultimate Route 66 Road Trip: Chicago to Santa Monica Pier

“Roads were made for journeys, not destinations.”

This quote perfectly encapsulates the essence of our fantastic road trip along the historic Route 66. Over five days, we embarked on a journey filled with adventure, exploration, and the pure joy of driving the legendary Mother Road.

Planning this trip wasn’t easy—it took nearly three months of research and careful consideration to decide on the perfect stops along the way. But all that effort was worth it, as each destination we chose added something special to our journey from Chicago to Santa Monica Pier, California.

Below are the highlights of the places we visited, each one contributing to the unforgettable experience of traveling one of America’s most iconic highways.

On June 30th, 2022, we embarked on an epic road trip along the historic Route 66, traveling from Chicago, Illinois, all the way to Santa Monica Pier in California. Known as the “Main Street of America,” Route 66 is a journey through the heart of the United States, filled with iconic landmarks, small towns, and a rich tapestry of American history. Our first day on the road was filled with excitement and discovery as we hit some of the most famous stops along the route.

Stop 1: Historic Route 66 Begin Sign, Chicago, IL

Location: 78-98 E Adams St, Chicago, IL 60603

Our journey began at the very spot where Route 66 starts—right in the heart of downtown Chicago. The Historic Route 66 Begin Sign is a must-see for anyone starting this legendary road trip. Standing at this iconic marker, we couldn’t help but feel the thrill of adventure as we prepared to travel the same road that countless others have driven before us. It was the perfect place to snap a few photos and mark the beginning of our journey.

Stop 2: Gemini Giant, Wilmington, IL

Location: S East St, Wilmington, IL 60481

Our next stop took us to Wilmington, Illinois, where we visited the Gemini Giant, one of the most recognizable roadside attractions on Route 66. This towering fiberglass statue of a spaceman holding a rocket is a quirky and fun reminder of the 1960s space race era. The Gemini Giant is a perfect example of the unique and nostalgic Americana you’ll find along Route 66. We spent some time marveling at this giant piece of pop culture history and snapped some memorable photos.

Stop 3: Cars on the Route, Galena, KS

• Location: Kan-O-Tex Service Station, 119 N Main St, Galena, KS 66739

As we continued our journey, we made our way to Galena, Kansas, to visit Cars on the Route, a restored Kan-O-Tex service station that celebrates the town’s connection to the Pixar movie “Cars.” The station features a collection of vintage vehicles that inspired characters from the film, including “Tow Tater,” the real-life inspiration for Mater. The charm of this small town and its ties to Route 66 made it a delightful stop on our trip. We enjoyed exploring the station and learning more about the history of Route 66 and its cultural impact.

Our first day on Route 66 was filled with iconic landmarks, a sense of nostalgia, and the thrill of adventure. From the bustling streets of Chicago to the small towns along the route, each stop offered a unique glimpse into the history and culture that make this road trip so special. As we continued our journey towards the Santa Monica Pier, we knew that this was just the beginning of an unforgettable adventure along the Mother Road.

Day 2: Journey Through Route 66 – From Stroud, OK to Amarillo, TX

On the second day of our Route 66 adventure, July 1, 2022, we continued our drive along the historic highway, making stops at some of the most iconic and fascinating sites along the way. The day was filled with a mix of classic Americana, history, and a bit of roadside fun.

Stop 1: Rock Cafe, Stroud, OK

Location: 114 W Main St, Stroud, OK 74079

We kicked off the day with a hearty breakfast at the Rock Cafe in Stroud, Oklahoma. This historic diner has been a staple of Route 66 since 1939 and is known for its rock walls and rich history. The cafe is not just a place to eat; it’s a slice of Americana that embodies the spirit of Route 66. The nostalgic atmosphere and delicious food made it the perfect place to start our day.

Stop 2: National Route 66 and Transportation Museum, Elk City, OK

Location: 2717 W 3rd St, Elk City, OK

Our next stop took us to the National Route 66 and Transportation Museum in Elk City, Oklahoma. This museum is a must-visit for anyone interested in the history of Route 66. It offers a comprehensive look at the Mother Road, complete with vintage cars, memorabilia, and interactive exhibits that transport you back to the heyday of Route 66. We spent some time exploring the museum, learning about the evolution of travel along the highway, and gaining a deeper appreciation for the significance of Route 66 in American culture.

Stop 3: Pops 66, Arcadia, OK

Location: 660 OK-66, Arcadia, OK 73007

After soaking in the history at the museum, we made our way to Pops 66 in Arcadia, Oklahoma. This modern roadside attraction is famous for its massive selection of over 700 different sodas and the iconic 66-foot tall soda bottle sculpture that lights up at night. We couldn’t resist picking up a few unique sodas to enjoy on the road, and of course, we had to snap some photos with the giant soda bottle that has become a beloved landmark on Route 66.

Stop 4: Cadillac Ranch, Amarillo, TX

Location: 13651 I-40 Frontage Rd, Amarillo, TX 79124

The final stop of the day was Cadillac Ranch in Amarillo, Texas. This quirky art installation is one of the most famous attractions on Route 66. It features ten Cadillac cars buried nose-first in the ground, all covered in layers of colorful graffiti. Visitors are encouraged to add their own graffiti to the cars, making each visit a unique and creative experience. We spent some time exploring the site, taking photos, and even leaving our own mark on the cars. It was a fun and memorable way to wrap up our day on the road.

Day two of our Route 66 journey was a blend of history, nostalgia, and creativity. From the historic charm of the Rock Cafe to the educational experience at the National Route 66 and Transportation Museum, and the modern fun at Pops 66, each stop brought something special to our adventure. Cadillac Ranch provided the perfect finale, allowing us to embrace the quirky, artistic side of Route 66. As we continued our drive towards Santa Monica, we couldn’t wait to see what else the Mother Road had in store for us.

Day 3: Exploring Natural Wonders – From Petrified Forest to Meteor Crater

On the third day of our Route 66 journey, July 2, 2022, we set out to explore some of the most fascinating natural wonders along the route. This day was all about experiencing the ancient history and geological marvels that make this part of the country so unique.

Stop 1: Petrified Forest National Park, AZ

We started our day at Petrified Forest National Park, one of the oldest national parks in the United States, known for its stunning collection of petrified wood. Walking through the park felt like stepping back in time, with ancient logs turned into stones scattered across the landscape. The park’s colorful badlands, ancient fossils, and remnants of prehistoric forests offered a glimpse into a world that existed millions of years ago. We spent the morning exploring the various trails, marveling at the vibrant colors of the petrified wood, and learning about the park’s rich history and geology. It was a truly mesmerizing experience that highlighted the natural beauty and historical significance of this incredible place.

Stop 2: Meteor Crater, AZ

• Location: Meteor Crater Rd, Arizona 86047

After leaving Petrified Forest National Park, we headed to Meteor Crater in Arizona. This massive impact crater was formed over 50,000 years ago by a meteorite collision, making it one of the best-preserved meteorite craters on Earth. Standing on the rim and peering into the bowl-shaped depression was truly awe-inspiring. The scale of the crater and the cosmic event that formed it left us amazed. The visitor center offered captivating insights into meteor impacts, allowing us to delve into the crater’s history and ongoing research.

Day three of our Route 66 adventure was all about connecting with the ancient past and marveling at the natural forces that have shaped our planet. From the prehistoric landscapes of Petrified Forest National Park to the cosmic impact site at Meteor Crater, the day was filled with awe-inspiring sights and profound moments of reflection. As we wrapped up our day, we couldn’t help but feel a deep appreciation for the incredible history and natural beauty that Route 66 has to offer. With more adventures ahead, we looked forward to continuing our journey along this legendary road.

Day 4: Discovering the Desert Wonders – Mojave National Preserve and Joshua Tree National Park

On the fourth day of our Route 66 adventure, we ventured deeper into the heart of California’s desert landscapes. July 3, 2022, was a day filled with the stark beauty of arid wilderness, from the vast expanses of the Mojave National Preserve to the otherworldly terrain of Joshua Tree National Park. The day ended with an unforgettable stargazing experience under the clear desert sky.

Stop 1: Mojave National Preserve, CA

Our first stop was the Mojave National Preserve, a vast and remote desert expanse that offered solitude and natural beauty. As we drove through, we were captivated by the open spaces, sand dunes, and mountain ranges. The preserve is home to diverse desert flora and fauna, including Joshua trees, creosote bushes, and coyotes. We explored some trails and appreciated the quiet majesty of the desert. The stark, untouched beauty of the Mojave Desert made a lasting impression on us.

Stop 2: Joshua Tree National Park, CA

After leaving the Mojave National Preserve, we made our way to the iconic Joshua Tree National Park. This park is famous for its unique landscapes, where the Mojave and Colorado deserts meet, creating an environment filled with the park’s namesake Joshua trees, massive boulders, and striking rock formations. We spent the afternoon exploring the park’s various trails, climbing the giant boulders, and marveling at the alien-like scenery that makes Joshua Tree so special. Each turn revealed a new and fascinating view, with the landscape shifting between forests of twisted Joshua trees and vast, open plains.

Stargazing at Joshua Tree National Park

As night fell, we stayed in Joshua Tree National Park to experience its magical stargazing. Known for its dark skies, free from light pollution, the park is one of the best places in California to observe the night sky. We found a quiet spot away from the roads, settled in, and watched the stars. The sky was breathtaking, with the Milky Way stretching across the horizon and countless stars twinkling above. It was a humbling experience, reminding us of the vastness of the universe and the serene beauty of the natural world.

Day four of our Route 66 journey was a celebration of California’s desert landscapes. From the expansive Mojave National Preserve to the enchanting Joshua Tree National Park, we were immersed in the rugged beauty and unique charm of these natural wonders. The day ended on a perfect note with an unforgettable stargazing experience that left us in awe of the desert night sky. As we prepared for the final leg of our journey to Santa Monica, we carried with us memories of the incredible sights and the peaceful solitude we found in the desert.

Day 5: Reaching the End of the Road – From Chicago to Santa Monica Pier

The last day of our incredible Route 66 journey marked the culmination of an epic adventure that took us from the heart of Chicago to the sun-kissed shores of California. On July 4, 2022, we completed our drive along Mother Road, arriving at the iconic endpoint—Santa Monica Pier.

Final Destination: Santa Monica Pier, CA

After days of exploring historic landmarks, natural wonders, and everything in between, we finally reached the end of Route 66 at Santa Monica Pier. Standing at the “End of the Trail” sign was a moment of triumph and reflection. The journey had taken us through a cross-section of America, from bustling cities and small towns to deserts and mountains, and now, here we were, with the Pacific Ocean stretching out before us.

Santa Monica Pier, with its vibrant atmosphere, amusement park rides, and beautiful beachfront, provided a fitting and celebratory end to our road trip. We took a moment to soak in the significance of completing this legendary drive, capturing photos at the famous Route 66 sign and enjoying the lively environment of the pier.

Reflections on the Journey:

Reaching the end of Route 66 was both exhilarating and bittersweet. The road had been our companion for five days, guiding us through a tapestry of diverse landscapes and cultures. Along the way, we experienced the charm of small towns, the awe of natural wonders, and the spirit of adventure that Route 66 embodies. Each mile brought with it new discoveries, and each stop added to the rich story of our journey.

Our Route 66 road trip from Chicago to Santa Monica was truly the adventure of a lifetime. It was a journey filled with iconic sights, unforgettable experiences, and a deep connection to the history and culture of the United States. As we stood at the end of the trail, we couldn’t help but feel a sense of accomplishment and gratitude for the memories we had made along the way.

Route 66 may be known as the “Main Street of America,” but for us, it became much more than that—it was a road of discovery, a path to new experiences, and a journey that will stay with us forever. If you’ve ever dreamed of driving Route 66, I can assure you that the adventure is worth every mile.

Key Locations (***)

1. Historic Route 66 Begin Sign, Chicago, IL:- 78-98 E Adams St, Chicago, IL 60603

2. Gemini Giant, Wilmington, IL:- S East St, Wilmington, IL 60481

3. Cars on the Route, Galena, KS:- Kan-O-Tex Service Station, 119 N Main St, Galena, KS 66739

4. Rock Cafe, Stroud, OK:- 114 W Main St, Stroud, OK 74079

5. Cadillac Ranch, Amarillo, TX:- 13651 I-40 Frontage Rd, Amarillo, TX 79124

6. 66 Diner, Albuquerque, NM:- 1405 Central Ave NE, Albuquerque, NM 87106

7. Petrified Forest National Park, AZ

8. Meteor Crater, AZ:- Meteor Crater Rd, Arizona 86047

9. Joshua Tree National Park, CA:- Joshua Tree, California 92252

10. Route 66 End Sign, Santa Monica Pier, CA:- 330 Santa Monica Pier, Santa Monica, CA 90401

Important Stops (**)

1. Pops 66, Arcadia, OK :- 660 OK-66, Arcadia, OK 73007

2. National Route 66 and Transportation Museum, Elk City, OK:- 2717 W 3rd St, Elk City, OK 73644

3. Mojave National Preserve, CA

Additional Points of Interest (*)

1. Blue Whale of Catoosa, Catoosa, OK:- 2600 OK-66, Catoosa, OK 74015

2. Conoco Tower Station & U-Drop Inn Cafe, Shamrock, TX:- 111 U.S. Rt. 66, Shamrock, TX 79079

3. Blue Swallow Motel, Tucumcari, NM:- 815 E Rte 66 Blvd, Tucumcari, NM 88401

4. Blue Hole, NM:- New Mexico 88401

5. Delgadillo’s Snow Cap, Seligman, AZ :- 301 AZ-66, Seligman, AZ 86337