From Chicago to Santa Monica, 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 really first heard of Route 66 from John Steinbeck in 1939. He called it “The Mother Road” in The Grapes of Wrath because he said he called farmers and migrants desperate for a new life during the Dust Bowl.

Route 66 took on new life after World War II when Americans had cars and money and time to travel. This road has symbolized the growth and evolution of America for more than 50 years. My wife, Pam, and I wanted to take this route and see these changes first hand – the history, the attractions, the nostalgia and the quirks.

So a few years ago she rode her Harley, and I rode mine, nearly 2,500 miles from Navy Pier in Chicago to Santa Monica Pier in California. It’s the ride we’re still talking about. This is the trip that we are still asked to do.

Learn from my mistake: you can’t do this trip justice without doing some homework. Find out about the route and the stops and choose those you want to make your trip special for you. There are plenty of traditional stops, like the Gateway Arch in St. Louis or the original McDonalds in Downey, CA. But I’m looking for the “different”. That said, let’s run through my top stops on Illinois Route 66 out west.

Spectacular wall art in the Pontiac
(Photo credit: Gimas / Shutterstock.com)

1. Pontiac Murals

Pontiac, Ill.

The pride of Route 66’s history is easy to see on the sides of buildings in downtown Pontiac, about 60 miles southwest of Joliet. Some of these works of art are truly spectacular and worth seeing.

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

2. Cars

Along the route

You’ll see many places along Route 66 that featured prominently in the Disney movie Cars. cars on the road is at 119 North Main Street, Galena, Kansas 66739. It is a former Kan-O-Tex gas station and parked in front is the International Harvester tow truck that inspired the Cars Tow Mater character.

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 at Shamrock for the best gas station photos. It’s big! And in Kansas, get up close for your photos with Mater. It’s funny.

The entrance to the Oklahoma City National Memorial
The time 9:01 is carved into the door at one end and represents innocence before the OKC explosion.
(Photo credit: northallertonman/Shutterstock.com)

3. Oklahoma City National Memorial

Oklahoma City

Many stops on Route 66 are special. This one was memorable and moving for me. I was on the news when I watched the scenes from the Murrah Federal Building that morning in 1995.

At the center of this magnificent memorial is a reflecting pool. The time 9:01 is engraved in the door at one end. It represents innocence before the explosion. The door with 9:03 engraved in it symbolizes the beginning of healing. The rectangular pool between them represents the moment of the explosion.

As I walked along this pool, I looked back and clearly saw the images of destruction and death. And closing my eyes, I saw the images of heroism and survival. To my right was a field of empty chairs. Nine rows of chairs signifying the floor where each of the victims died. And there are 19 smaller chairs — for children who died.

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

Pro tip: Get there before 9 a.m. and allow travel time for rush hour traffic. I hope standing there at 9:01 a.m. is as emotional 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 on the historic route, provides perspective on history and an appreciation of its significance.
(Photo credit: Rosemarie Mosteller / Shutterstock.com)

4. Oklahoma Route 66 Museum

Clinton, Oklahoma

Several states have Route 66 museums and each details the local impact of the route. The one that struck me the most happens to be the tallest and has changing exhibits that showcase the highway. Keep in mind that at this point in your tour of Route 66, you will have some perspective on history and appreciate its significance.

Pro tip: Just in front of the museum is the Inn of the trade winds. Clinton is halfway between Memphis and Las Vegas. Elvis and his entourage stayed there four times. He’s always had room 215. The hostel keeps room 215 as it was, and you can see it. Thank you, thank you very much.

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

5. Sandhills Curiosity Shop

Eric, Oklahoma

This place just cracked me up. Street signs, vintage guitars, antique furniture, bric-a-brac, memorabilia, and things that I find hard to categorize are piled high in this store where nothing is for sale. Rather, it’s a quirky museum claiming to be 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 her quirky humor and live music, which might not be suitable for younger ears.

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

6. Cadillac Ranch

Amarillo, TX

This is an art exhibition where you are encouraged to add your own graffiti! West of Amarillo, grab a spray paint can and add your flair to one of 10 caddies buried nose-first in a field. An eccentric millionaire paid artists to create it in the mid-1970s, so it’s part art project, part avant-garde sculpture garden, 100% weird, 110% memorable. You are on I-40 at this point in the journey, 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 skies at these times make great backdrops for photos, cars and, of course, you! You must bring your own spray paint and flashlight. There are no lights and you will walk on a flat dirt road for about 50 meters to get to the partially buried cars. Parking is along I-40 Frontage Road.

Texas, the Mid Point Cafe on Route 66
This cafe is exactly where you’d expect it to be – half way down the road.
(Photo credit: Gimas / Shutterstock.com)

7. Route 66 Mid Point Cafe

Adrian, Texas

This cafe is exactly where you’d expect it to be – half way down the road. Even if you don’t have a sweet tooth, trust me, stop by the self-proclaimed “Home of Ugly Pies”. To be honest, I don’t remember what they tasted like, but the piece(s) I had tasted were excellent!

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

8. The Wigwam Motel

Holbrook, AZ

It was the Airbnb of its time! Route 66 gave birth to “motor hotels” and these became “motels”. They were built near the road, unlike the expensive traditional hotels that were found in city centers. These wigwams have bathrooms, showers, heating, air conditioning and cable. You will have to live without Wi-Fi for one night. Rates are under $100, but book ahead.

Pro tip: Don’t miss a great photo op with some of the classic cars parked outside the rooms as they were decades ago.

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

9. Standing in a corner

Winslow, Ariz.

Sounds like a song, right? The classic song from the Eagles hit “Take It Easy” is another photo op just waiting for you. The mural on the building on the corner of Kinsley and E2n/a Winslow Street is that of a storefront reflecting “a girl, my Lord, in a flatbed Ford slowing down to look at me”.

Pro tip: Due to the layout and size, it’s not an easy place for selfies. Try it the old fashioned way. Ask someone to take the picture for you. Street parking is easy and close.

I’d like to show you the great old neon signs and vintage motels in Tucumcari, New Mexico. Or share my photos of historic buildings and retro signs in Santa Rosa, New Mexico, or old gas stations – some renovated, some sadly withered with time. I love this road for its history, its little piece of Americana and what it says about our century and how we grew up as America and Americans.

My best advice is to do this homework. There are many books and apps to help you. Be sure to lower the hood and remember that it’s not a matter of destination, whether it’s Chicago or Los Angeles. It’s a matter of travel. Let it sink in.

Breathe. Or two. Place the smartphone in the center console and concentrate on the road. You are now ready to start writing your own Route 66 stories. See you on the road.

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