On The Road Again: Route 66 Chicago to Winslow

Standing on the corner in Winslow, Az

While the October/November weather was still holding, we decided to take another road trip in the Challenger; Chicago to Winslow, Arizona via the historic Route 66. A few years ago we drove  Route 66 from Vegas to Flagstaff and I wanted to drive more of this historic road before it completely disappeared.
There are plenty of sights to see during this 15-day round-trip drive. We also made a detour off the route to visit a couple of National Parks and Monuments. You know,  since, we were so close.
We didn’t stay on RT 66 the entire time because Interstate 40 runs parallel to it quite frequently.  I-40 replaced much of  RT 66 and in many cases runs parallel to the original road as a frontage road.
Our goal during planning was to drive about 400 miles every day and stop along the way at things that interested us or were suggested by the guidebooks and maps that we were following.
I put a list of the resources that we used at the end of this blog.

Route 66 was the first continuous road built from Chicago to L.A. back in 1933. It became known as the Main Street of America. It goes through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California. It is 2,448 miles long and passes through the southern states to avoid harsh winter conditions. In 1933, it was paved with Portland cement and was a fully functional, federally funded highway that endured for fifty years. It was decommissioned in 1985 and replaced by three separate interstate highways which bypassed many of the small towns.

During RT 66’s heyday in the 30’s,’40s and ’50s, gas stations, motels, and Mom and Pop dinners opened up along the route to serve and cater to the motorists that were driving to California.
After WWII, the GIs came home with time and resources. The “Rust Belt” of the Midwest had run its course and opportunities in California became more abundant. California’s sun, ocean, and the LA area were the place to be and RT 66 provided the means to get there.

The romance of the open road, the promise of freedom and the lure of what we can dream about lies beyond the horizon. The love affair with the American automobile was born and inspired by car designs that transcended beyond Henry Ford’s Model A.

In the late 1950s, parts of the route were starting to be replaced by President Eisenhower’s project to build highspeed highways to increase commerce as well increase the mobility of the U.S. military. As always, progress and modernization always result in some kind of displacement. Many of the businesses that served the motorists like the Mom & Pop stores, motels, and gas stations slowly went out of business beginning in the ’60s as the interstates bypassed many of the small towns. The Disney movie “Cars” tells a fictional story based on the real towns and people along this famous route.

Bottom Line #1.
The original route was fully functional for just fifty years.
The fifty-year love affair with the automobile has shaped our nation, our culture, and our commerce.

A lost section located in the boundaries of Petrified Forrest National Park

Parts of the original route are no longer maintained and have been absorbed into the landscape.
Other parts have been renamed and are part of the local county roads, while other parts are being preserved, restored, and celebrated by enthusiasts and associations in each of the states that the historic road passes through.

Notice the telephone poles and compare to the lost section photo

Today, Route 66 represents a slice of Americana. It’s why people come from all over the world to drive it, to experience it. For many car enthusiasts, driving Route 66 is a bucket list item. The romantic lure and freedom of the open road continue to draw people to make the slow travel drive. During our many stops and historic sights along the way, curators of the Route 66 pop culture icons asked us to sign the visitor’s book. The book is filled with visitors from as far as Australia, New Zealand, and Europe, as well as people from around our very own country.

We prepared for the trip by picking up travel books from the local library. Mrs.fromthebachrow also picked up information about the route from a few of the state agencies. Oklahoma Department of Tourism surprised me with a beautiful Route 66 booklet chockfull of detail and very useful information.

If you have a goal to visit every state in the country, and you need some leverage to get to Oklahoma, then Route 66 is your answer.
Here are a couple of useless trivia factoids that stick in my mind.
a. Tulsa was used as a scene location for filming the 1983 movie The Outsiders.
I still remember that movie with Patrick Swayze, Tom Cruise, Matt Dillion, Ralph Macchio, Rob Lowe, Emilio Estevez, C. Thomas Howell, and Diane Lane. If you’re a movie buff and interested in seeing these “kids” before they were famous, then check out this movie.
b. Jack White lives in Tulsa.
c. Jason Lee (the skateboarder and actor) is shooting a new series in Tulsa. He also has a book of photos that showcase Tulsa.
d. Tulsa has the second largest collection of Art Deco architecture in the U.S. second only to Miami Beach.

Route 66  Oklahoma sites and roadside attractions are just as interesting if you’re into old diners, gas station motels, and car travel nostalgia.

Bottom Line #2. 
Oklahoma has more drivable miles of Route 66 than any other state. 374 miles to be exact.

We took a 286-mile detour off of RT 66 at Tucumcari, NM to visit Carlsbad Caverns National Park and White Sands National Monument, NM.

white gypsum sand

One of the things that I read in many of the travel books was the suggestion of filling up your gas tank when it reaches a half a tank. Being a city/ suburbanite, I didn’t think much about this advice as my reference point is a gas station every 2 miles, with two on each corner.

Bottom Line #3.
Before driving through the deserts of New Mexico, top off your gas tank. Towns are sometimes far and few between en route to your next destination.

No, I never ran out of gas. I realized how important that piece of advice was driving the stretch between Oklahoma City, OK to Amarillo, TX. There were long stretches of road that offered few exits and opportunities for fuel. The Challenger R/T was getting 28 mpg at a cruise speed of 82 mph with good gas. No, I was not speeding, the posted speed limit was 75 mph. I was merely keeping up with traffic, really.

Not all gas was “good” for the R/T. Sometimes, I had no choice but to use gas that contained “Up To 10%”  Ethanol.  With ethanol in the mix, gas mileage varied between 22-26 mph.  Now granted we were slowly climbing the road up to the continental divide altitude at speed. The tachometer demonstrated that the car was working slightly harder going up. It’s the gradual downward grade that I notice the performance of the gas with ethanol.

On the road to Carlsbad, NM, there was a stretch of NM RT 54 that was long straight, and flat that reached far past the horizon on a sunny 65° day. The desert scenery was nothing but scrubland. No houses, side roads, water, birds or any kind of road kill along this route. One could see a car coming from 10 miles away, and we only encountered a couple.

The vastness of the desert in our country is something to see and experience in a vehicle other than an airplane.

After about 50 miles on this road, I felt pretty confident that nothing was going to jump out of the brush, nor was there a car in sight. So I decided to take the Challenger up past 120 mph on the longest, smoothest, flattest straightest road that I have ever driven on. 80/90 mph is pretty easy for me. 100 mph gets my heart and adrenaline pumping. I have experience with the car at 112 mph for a few seconds from when she was new. I trusted the stability of the car at “my own self-imposed ludicrous” speed.
On a road like this, there are no environmental visual indicators to judge one’s speed. The physical indication at high speed is road/air noise and the sound of the engine.
After I saw that I hit 120 mph on the speedometer, I focused on the road and let her run a bit without checking the final speed reading. The car was still pulling and I could feel that she could make it up to the programmed speed limiter of 130 mph. Top factory programmed speed on my car is 130 mph due to the speed rating on the factory tires. The tires that I have mounted now are rated for 150 mph. (No, I’m not interested in tuning her to achieve the 150 mph tire speed limit.)

New Mexico desert highway
Magnificent Desolation

I was pretty happy with 120+ mph with a trunk full of luggage and a passenger firmly strapped in her seat with perfect posture, feet firmly braced to the floor and head pinned against the headrest. Mrsfromthebachrow was happy that my 3 minutes of fun had safely come to an end. There’s no need or desire to get this particular car past 100 mph again.
I am interested in joining the 200 mph club, and that will take some training, planning and the right vehicle in the future.

There were plenty of preserved and restored gas stations along the way. They operate now as tourist info stops, gift shops or museums. There are even several fully functional diners where we stopped at for lunch or dinner. Each one was chock full of nostalgic photos and memorabilia that made this route so famous.

Shamrock, TX
Wellston, OK

There was also a fair amount abandoned buildings that were shells of former businesses that at one time served the many travelers of the time. I decided that I did not want to document the decay in photos of these once fine establishments and tourist traps and focus instead exclusively on neon and shiny refurbished items.

There are the oddities along RT 66 that keep the road eclectic and contemporary with a nod to its fabled past. Cadillac Ranch, Pops On Route 66 and The Blue Whale. All of these attractions become part of “The Mother Road’s” storyline.

Cadillac Ranch
Pops on Route 66

We stopped at one of the curators of the RT 66 history. Classical Gas Museum in Embudo, NM has an amazing collection all things Old Automotive and old gas pumps that the owner, Johnnie restores and sells. He is a genuine and wonderful Route 66 character who takes so much pride in salvaging and restoring many of the treasures long forgotten or lost in salvage yards. The old S&H Green Stamp dispenser that I remember from retail stores caught my eye and triggered many memories of my youth. He even had the S&H Green Stamp catalog that I was thumbing through. I now know where my Mom got her Aluminum Turkey Roasting pan that is still in the family.

waiting for restoration
Taos County, NM

There are car people and there are not.
For the car people, the drive along the entire stretch of RT 66 is the trip of a lifetime, if you are into nostalgic Americana. If not, and you find yourself “antiquing” near or along towns that support the Route 66 culture, slow down and stop at a dinner. You will never know what memories of your youth will be stirred up that will surely bring a youthful smile.

Driving while the sun sets on Route 66

Bottom Line #4.
Here are a few of the guides we used along the way. Each will provide you with the necessary tips and tricks to get the most out of your RT 66 experience. The first two were invaluable as Mrsfromthebachrow was perfectly navigating some of the lost stretches of the route.

Route 66: EZ66 Guide For Travelers- 4th Edition Spiral
Jerry McClanahan

Here It Is! The Route 66 Map Series
Jim Ross and Jerry McClanahan

Route 66 Road Trip USA
Jamie Jensen

We also visited Carlsbad Caverns National Park, White Sands National MonumentPetrified Forest National Park, and Tent Rocks National Monument
These parks are tucked away off the beaten path and well worth the visit and experience.

Thanks for reading.
Comments and passing this blog along to friends would be very appreciated.

Author: Francis

Started out in science and somehow ended up in sales & marketing. Grew into a results oriented sales professional with extensive experience selling and positioning scientific solutions in the pharma/biotech, life sciences and medical diagnostics markets. In 1998 I created an excel sheet to track spending and cash flow to learn personal finance on my own. They don't teach this in school and by the time one figures it out, most of let all these resources slip through our fingers. It's time to pay it forward to this next gen so that they can shave 15-20 years off for working for "the man" with insights, a library of tools, and motivation from me and plenty of other FI bloggers that I follow.

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