Chicago to Santa Monica, the 9 best stops on Route 66

Chicago to Santa Monica, the 9 best stops on Route 66

If you look for it on a map, it doesn’t exist. The federal government removed Route 66 from the US Highway System in 1985.

America first learned about Route 66 from John Steinbeck in 1939. He called it “The Mother Road” in The Grapes of Wrath because he said it called farmers and migrants desperate for a new life during the Dust Bowl.

Route 66 took on a new life after World War II when Americans had cars and some money and time to travel. For more than 50 years, this street has symbolized America’s growth and change. My wife Pam and I wanted to drive this road and see these changes first hand – the history, the attractions, the nostalgia and the oddities.

So a few years ago she rode her Harley and I rode mine almost 2,500 miles from Navy Pier in Chicago to Santa Monica Pier in California. It’s the ride we’re still talking about. It’s the journey we’re still being asked about.

Learn from my mistake: you can’t do this trip justice without doing some homework. Read more about the street and the stops and choose which one she want to make your trip special. There are many traditional stops, like the Gateway Arch in St. Louis or the original McDonalds in Downey, California. But I’m looking for the “other”. However, let’s drive my top stops on Route 66 west from Illinois.

The spectacular mural at Pontiac
(Image credit: Gimas / Shutterstock.com)

1. Pontiac Murals

Pontiac, Illinois

Much pride in Route 66’s history can be easily seen on the sides of buildings throughout downtown Pontiac — about 60 miles southwest of Joliet. Some of these works of art are truly spectacular and worth a walk or drive.

Pro tip: The Route 66 Association Hall of Fame and Museum is the best place to start for mural maps. You can find the hall at 110 W Howard St, Pontiac, IL 61764.

2. The cars

Along the route

You will see many locations along Route 66 that played a major role in the Disney film cars. Cars On The Route is located at 119 North Main Street, Galena, Kansas 66739. It’s an old Kan-O-Tex gas station and it has the International Harvester tow truck that was the inspiration for it out front cars Character Tow Mater.

I loved the beautiful art deco gas station at 101 E. 12th Street Shamrock, Texas. It is at the intersection of US 83 and Route 66.

Pro tip: Park across the street in Shamrock for the best pics of the gas station. It is big! And in Kansas, Mater lets you get up close and personal with your pictures. It is fun.

The entrance to the Oklahoma City National Memorial
The time 9:01 is engraved on the gate at one end, representing the innocence before the OKC explosion.
(Image credit: northallertonman / Shutterstock.com)

3. Oklahoma City National Monument

Oklahoma City

Many stops on Route 66 are special. It was unforgettable and moving for me. I was on the television news watching the scenes from the Murrah Federal Building that morning in 1995.

In the center of this beautiful monument is a reflecting pool. The time 9:01 is engraved on the gate at one end. It represents innocence before the explosion. The gate with the 9:03 engraved in it symbolizes the beginning of healing. The rectangular pool in between represents the moment of the explosion.

As I walked along this pond, I looked back and clearly saw the images of destruction and death. And as I closed my eyes I saw the images of heroism and survival. To my right was a field of empty chairs. Nine rows of chairs mark the floor on which each of the victims died. And there are 19 smaller chairs – for the children who have died.

On the rest of the wall of the building is a plaque with the names of the 600 survivors that day. The Oklahoma City National Memorial is incredibly moving. Of all the memorable stops on our trip, this one is on my top spots list because it impressed me so much. I encourage you to take the time to stop…and really stop remembering.

Pro tip: Get there before 9:00 AM and allow for travel time for rush hour traffic. I hope standing here at 9:01 am is as moving for you as it is for me.

The Oklahoma Route 66 Museum is operated by the Oklahoma Historical Society, Clinton, OK
This Route 66 museum, the largest along the historic route, provides insight into history and celebrates its importance.
(Image credit: Rosemarie Mosteller / Shutterstock.com)

4. Oklahoma Route 66 Museum

Clinton, Oklahoma

Several states have Route 66 museums and each showcases the local impact of the road. The one that struck me the most happens to be the largest and has rotating exhibits highlighting the Autobahn. Remember, at this point in your Route 66 tour, you will have an insight into its history and an appreciation for its importance.

Pro tip: The Trade Winds Inn is directly across from the museum. Clinton is about halfway between Memphis and Las Vegas. Elvis and his entourage stayed there four times. He always had room 215. The inn keeps room 215 as it was and you can see it. Many Thanks.

Sandhill's Curiosity Shop
Erick’s oldest building, the Sandhills Curiosity Shop
(Image credit: StockPhotoAstur / Shutterstock.com)

5. Sandhill’s Curiosity Shop

Eric, Oklahoma

This place just blew my mind. Street signs, vintage guitars, antique furniture, junk, memorabilia and things that I have trouble categorizing are piled high up in this nothing-for-sale store. It’s more of a quirky museum that lays claim to being the “redneck capital of the world.” Give it an hour and let me know how you describe it.

Pro tip: Harley Russell runs the place and entertains with his offbeat humor and live music that may not be suitable for younger ears.

Cadillac Ranch, Amarillo, Texas
Part art project, part avant-garde sculpture garden in Amarillo, Texas
(Image credit: Cheryl-Annette Parker / Shutterstock.com)

6. Cadillac Ranch

Amarillo, Texas

This is an art exhibition where you are encouraged to add your own graffiti! Just west of Amarillo, grab a can of spray paint and give your flair to one of the 10 caddies buried nose-first in a field. An eccentric millionaire paid artists to create it in the mid-’70s. So it’s part art project, part avant-garde sculpture garden, 100 percent weird, 110 percent memorable. You are on I-40 at this point, so look for exit 60 and take it to 13651 I-40 Frontage Rd, Amarillo, TX 79124.

Pro tip: I suggest going at dawn or dusk. The sky at these hours creates great backdrops for the pictures, the cars and of course you! You must bring your own spray can and flashlight. There are no lights and you walk about 50 meters down a flat dirt track to get to the partially buried cars. Parking is located along I-40 Frontage Road.

Texas, the Mid Point Cafe on Route 66
This café is exactly where you would expect it to be – halfway down the route.
(Image credit: Gimas / Shutterstock.com)

7. Route 66 Mid Point Cafe

Adrian, Texas

This café is exactly where you would expect it to be – halfway down the route. Even if you don’t have a sweet tooth, trust me, stop by the self-proclaimed “Home of Ugly Pies.” To be honest I can’t remember what they looked like but the pieces I had tasted great!

Pro Tips: There is a good photo opportunity at the sign halfway across from the cafe. And again: TRY. THE. CAKE.

8. Wigwam Motel

Holbrook, Ariz

This was the Airbnb of its time! Route 66 spawned “motor hotels” and these became “motels”. They were built close to the street, as opposed to the expensive, traditional hotels that were downtown. These wigwams have bathrooms, showers, heating, air conditioning and cable. You have to get by without WiFi for a night. Prices are under $100 but book in advance.

Pro tip: Don’t miss a great photo op with some of the vintage cars parked in front of the rooms like they were a few decades ago.

The classic from the Eagles hit “Take It Easy” is another photo op just waiting for you.
(Image credit: Mark Skalny / Shutterstock.com)

9. Standing on a corner

Winslow, Arizona

Sounds like a song right? The classic from the Eagles hit “Take It Easy” is another photo op just waiting for you. The mural on the building at the corner of Kinsley and E2nd Street in Winslow has a window displaying “a girl, my lord, in a flatbed Ford, slowing down to look at me”.

Pro tip: Because of the layout and size, this isn’t an easy spot for selfies. Try it the old fashioned way. Get someone to do the recording for you. Street parking is easy and close by.

I’d love to show you the grand old neon signs and vintage motels in Tucumcari, New Mexico. Or share my pictures of historic buildings and retro signs in Santa Rosa, New Mexico, or of the old gas stations – some remodeled, others sadly withered over time. I love this street for its history, its little slice of Americana and what it says about our century and how we’ve grown as America and Americans.

My best advice is to do this homework. There are tons of books and apps to help you with this. Make sure you put the top down and remember that it’s not about the destination, whether it’s Chicago or LA, it’s about the journey. let that sink

Get some air first. Or two. Place the smartphone in the center console and focus on the road. Now you’re ready to start writing your own Route 66 stories. I’ll see you on the way.

Destination Santa Monica? Watch how to spend a day in Santa Monica and rediscover California: How a writer learns to love the place where she lives again.

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