5 Ways to Prepare Kids for a Route 66 Road Trip

When planning for our road trip, I took some advice from one of my favorite books called The Art of Travel by Alain de Botton. His essay “On Anticipation” is especially pertinent and enjoyable, especially for a road trip with kids. In it, he says that a major part of the joy of traveling is the anticipation of one’s journey. And I agree.

Fun Family Travel

The Importance of Anticipation

The importance of the anticipation of a trip cannot be overstated. Travel is not just what occurs moment to moment on a journey. It is the excitement and the anxiety, the planning and the preparation, the feeling of “Are we really going to do this?” Not only that, but it is also the interplay of one’s expectations with reality. Sometimes the reality is worse than the expectation, but more often than not, the traveler encounters a reality that she never could have imagined. The surpassing of what one can imagine with the majesty of the reality that one can actually encounter is what we all hope to experience on an epic trip. The only way this is possible is to prepare for the trip intellectually.

A major part of the joy of traveling is the anticipation of one’s journey.

As adults, we tend to do this on our own without any prompting from the outside world. We look at maps, perhaps do some research. We buy our tickets and (sometimes) plan out where we will be sleeping. We have to do this otherwise there would be no journey upon which to embark.

Route 66 Kansas
The kids having one of many pajama days.

Children, on the other hand, are a whole different story. They just do what we adults tell them to do. Sometimes they cry and fight, and sometimes they listen willingly. But we, as parents, would be remiss if we didn’t offer our children the chance to prepare their awesome little brains in the same enriched manner that we, with all our lifetimes full of experiences, can prepare.

We helped our little ones prepare for our Route 66 road trip in the following ways:

  1. We posted up a roadmap of the United States and traced (as best as we could) the route that we would be taking on our travels.
  2. We visited websites together and looked at pictures of things we were hoping to see along the way. We even found a site called Kidson66.com that had some nice coloring pages that I stapled into a book for the kids.
  3. We re-watched the movie Cars and talked about the significance of the old road versus the new highway, taking into consideration both the positives and negatives of progress and change.
  4. We purchased children’s travel journals. Though we weren’t so faithful in documenting our trip while we were traveling, the prompts on the preparation pages helped the children allay some anxiety and express some expectations and hopes.
  5. We bought kid-proof cameras so the children could take pictures of important events and sites that they wanted to capture. (I also had a selfish reason for doing this. I wanted to be able to see the trip from their perspectives. And they took some really amazing pics!)

Preparing children for a trip like this will help everyone enjoy their travels. Especially on a trip like the one we took, where the answer to the question “Are we there yet?” is perpetually “No.” We were going on a journey to embark upon an adventure, not to get to a final destination. It was important the children knew and understood this concept. Whatever your purpose, make sure your children are prepared and know what to expect. But also make sure they are prepared to expected the unexpected. After all, that’s the best part.

Why Should Your Family Take a Route 66 Road Trip?

Who’s idea was this Route 66 trip anyway? Do we really want to spend this much time in a car, with kids, trying to capture a look into the past? … It looks broken down to me…

–My Husband

Route 66 Illinois

I think everyone thought I was crazy when I decided that our family was going to embark on an epic road trip exploring Route 66 with kids. And that my ultimate goal was to make it all the way from Chicago to Santa Monica and back in 11 days.

Why Route 66? I really have no idea. I pretty much shared my husband’s above sentiments about the old road.

But I knew I had a goal in mind… Two goals actually: 1) To see the Grand Canyon, and 2) To make it to the Pacific Ocean. Other than that, whatever happened along the way would happen.

Sunset over the Pacific Ocean

So, why Route 66 with kids? Especially when one of those two little kids was completely averse to car travel? Well, my answer is, that’s exactly why. I wanted my overly-sensory son to experience the discomfort so he could discover the amazing things that could happen if he could just let go a little. In fact, I wanted that for all of us. We had all grown a little too comfortable with our lives in the suburbs. And I, especially, felt that I had reached a time in my life when I would explode and maybe leave some collateral damage behind if I couldn’t find a way for the family to burst out of our comfort zone together.

Mater Route 66
The kids with life-sized Mater in Galena, KS.

We had all grown a little too comfortable with our lives in the suburbs.

Another reason to explore Route 66 is because of the simple fact that a very popular children’s movie (you know the one I’m talking about) addresses the importance of the old road and the changes that growth and capitalism can affect – positive or negative. I am definitely one who lives to tie in life lessons with popular culture (and math lessons, and science lessons, and all kinds of lessons). After all, children and adults alike are already familiar with popular culture. Comparing pop culture with new ideas makes the new ideas more accessible, and imbues the things we all experience in everyday life with so much more meaning. Does that make sense?

Yet another reason for Route 66 is that our family started calling the summer of 2016 the Summer of 6! The twins were 6, we purchased season passes to Six Flags, the year 2016 ended in a 6, so it only made sense to explore The Mother Road, Route 66.


To recap, the reasons we took this road trip:

  1. To see sites that my husband and I had talked for years about seeing, but always disregarded our wanderlust for home, work, and school responsibilities.
  2. To help my overly-sensitive son to overcome some of his discomfort and fear with experiences in everyday life.
  3. To break our family out of a comfort zone that was stifling our zest for life.
  4. To help my children learn the real story behind the fiction of one of their favorite children’s movies.
  5. Because it was the Summer of 6 for our family!

All that said, we had an amazing trip. Despite the fact that there is a dearth of information out there about where Route 66 actually is and how to travel with 6-year-olds! On this website, I will share resources that we used to make our trip successful and the routes that we took.

One last thing…

Especially when traveling with children, it’s important to remember that your trip is YOUR trip. Don’t let anyone tell you what you should and should not do during your trip. Route 66 is a very old road with lots of starts and stops. We did not stay 100% faithful to traveling ON Route 66 the whole way. We had limited time and our children had limited patience, especially for the 10-12 hour drive days. Route 66 symbolizes the freedom to explore our nation, the freedom that technology has given us, and the freedom that we all need to feel. And we all should feel free to explore in the way that works for each of us!