sixtyandme logo
We are community supported and may earn a commission when you buy through links on our site. Learn more

We Got Our Kicks on Rt 66!

By Cynthia Hogg February 02, 2023 Travel

What Baby Boomer doesn’t know at least the refrain from Nat King Cole’s rendition of “Get Your Kicks on Rt. 66”?

Rt 66. The “Mother Road.” Neon signs, motels, offbeat and over-sized roadside attractions.

Growing up in the 50s and 60s, I criss-crossed the USA on summer vacations with my family, and we traveled along several sections of “America’s Highway.” I remember seeing the signs for Meramec Caverns painted on the sides of barns, clustering ever thicker the closer we got.

During our trips we shared the road with hundreds, perhaps thousands, of similar families, young parents proud of their shiny station wagons filled with their personal contribution to the post-war Baby Boom.

Perhaps in the midst of the present craziness, a desire to return to simpler times is understandable. Maybe nostalgia is unavoidable at my age. All I know is when I turned 66 last spring, I experienced a sudden desire to travel Rt 66. It had to be this year. After all, not only was I now 66, but I had a six-year-old granddaughter. Would her parents let me take her on a slightly crazy 4-day road trip? Why yes, they would!

Where to Start from?

I did realize I couldn’t pack up a six-year-old child and drive 2,448 miles from Chicago to LA – and then back again – so I decided we would do 1/6 of Rt 66. I calculated that to be about 408 miles, which seemed very doable.

Having no desire to start at the very beginning in downtown Chicago (I don’t drive in Chicago if I can help it), we picked Joliet, Illinois, as our starting point. Joliet has many Rt 66 museums and attractions and it is apparently a common starting point for travelers who are willing to pass on the small official starting point sign in downtown Chicago.

Not That Simple a Trip

408 miles would take us roughly to Devil’s Elbow, Missouri. I say “roughly” because traveling Rt 66 is far more complicated than I had first realized. I had no idea! Turns out Rt 66 never was one completely straightforward path from Chicago to LA anyway. New alignments were constantly popping up.

On our trip I would find myself on the 1926–1930 section, and then a 1930–1940 section, and then a 1945 section. I bought a Rt 66 spiral-bound guidebook and consulted it constantly to make sure I was staying on the right road.

Sometimes Rt 66 joined a modern divided highway. Hallelujah! I could make up some of the time I lost from all the wrong turns I made on the country roads, and it didn’t feel like cheating!

The Blues Brothers on the roof of the Rich ‘n’ Creamy Ice Cream Shop in Joliet saluted us as we set off. We started by making a wrong turn out of the parking lot of Rich ‘n’ Creamy and lost about 20 minutes right from the get-go. Ha!

This didn’t bode well for our trip, but I made up my mind that while we’d do our best to follow this crazy, mixed-up piece of nostalgia for four days, if we occasionally got lost, who cares? We’d still be having fun because we’d be together.

Roadside Attractions Keep Kids Active

My granddaughter was immediately captivated by the kitschy roadside attractions, as our first stop after leaving Joliet was the Launching Pad drive-in with its “Gemini Giant,” the first of many larger-than-life attractions we saw along the way, including a huge covered wagon with a massive Abraham Lincoln, a giant rocking chair, and a 40-foot bottle of ketchup.

Simply not the sights typically seen when zipping along a modern freeway! My granddaughter kept a lookout for the Rt 66 road markers along the route. She loved this – and it turned out to be a very important job!

Authentic-from-the-Era Diners and Motels

We tried to hit authentic-from-the-era restaurants. Our favorite was the “Cozy Dog” in Springfield, IL – home of the original corn dog on a stick. We saved our French fries from the Cozy Dog for a photo-op with the 40-foot ketchup bottle later in the day. Fun! Another favorite meal was breakfast at Shelly’s Rt. 66 Café in quaint Cuba, Missouri.

I knew I also wanted to stay in authentic-from-the-era motels. On our second night, we hit the jackpot with the Wagon Wheel Motel, the longest continuously-run motel along the entire route, wonderfully restored and maintained.

On our last night, we stayed in the Carlin Villa in Carlinville, IL – a typical bare bones motel from the era. Nothing fancy, no indoor pool or exercise room, but the room was spacious, and I loved the old-fashioned room key!

A Bonus Along the Way?

Meeting other people making a similar trek. Turns out that traveling Rt 66 when turning 66 is a rite of passage for many Baby Boomers. Who knew? I thought I had dreamed up the idea all by myself!

All the volunteers we met at the various museums were so knowledgeable and eager to share. All along the way, I got the sense that the locals were quite proud of their part in the past and present history of the Rt 66 saga.

By the end of our travels, we were definitely tired. We had traveled nearly 1300 miles in 3-1/2 days. My brain hurt from all the navigating, but my heart was full. I know this is a trip my granddaughter will remember her whole life.

Now my other grandchildren are jealous and want their turn to travel Rt 66. Hmmm. I have 10 grandchildren and five-sixths of the route still unfinished. I just might be able to complete the whole thing! With a grandchild or two in tow, who says Rt 66 wouldn’t be just as much fun at age 67, 70 or even 75?

Let’s Have a Conversation:

Have you traveled any or all of Rt 66 back in the day? What about a recent trip? What were your favorite sights? If you haven’t gone, what would you most like to see?

Notify of

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Inline Feedbacks
View all comments

I haven’t gone yet, but Cynthia’s great story makes me want to! What a wonderful memory she has created with her sweet little granddaughter! No grandchildren yet for me, but maybe I can rope one of my kids into going with me.


Travelled 66 from Amarillo to Chicago when my now 27-year-old granddaughter was 5. Prepped her by getting the American Girl book “Molly’s 66 Adventure,” so she loved seeing the iconic landmarks featured in the book come to life! That trip, along with several subsequent road trips with just the two of us, have become what she describes as her favorite childhood memories.

Katherine S

Thanks for sharing! Driving Route 66 has always appealed to me — less so for my spousal unit. Perhaps less daunting in stages. Hmmmm.

Joan Callahan

Very fun article, but don’t leave out Chicago! I am 72 and live two blocks from that seminal corner and it is a great place to start. Between the Bean, music, museums, and lakefront parks, it safe (ignore the media bashing) and easy to get around. Traveling the country is just a wonderful way to be with family as you describe so well.

Deb S

What a wonderful experience! I will be 66 next fall, so am going to research this! Thanks for sharing.

Donalee Davis

Loved this article. We have been on 66 many times. From New Mexico to Tennessee. Stayed in several 66 motels. Hope you get to take more grandchildren on 66.

1 2 3

The Author

Cynthia Hogg is a freelance writer in western Michigan who contributes regularly to Sixty and Me and Senior Perspectives magazine. She loves to travel and spend time with her grandchildren, especially combining the two. She is the editor of the newly updated blog

You Might Also Like