With so many people planning their own Route 66 trips, I thought I would share a number of my random thoughts and lessons learned from our trip taken over sixteen days back in September and October last year.

In my previous post I talked about our planning process so now I’ll talk about what we learned along the way and how our actual execution varied from the plan. These are in no particular order, but rather my thoughts as they come to mind.

Route 66 Will Be Different For Everyone and That’s Okay

I mention this both as a tip for your own trip as well as a disclaimer for this post. “Your mileage may vary.” Everyone comes onto Route 66 with different interests, different timelines, different backgrounds, different means of transportation, and different expectations. Route 66 is a personal experience and you will need to customize it for what interests you the most.

For example, we focused our trip on the classic motels. We love the quirkiness of the individually owned places and the history of motels which have been welcoming travelers for decades. This worked for us and we loved it, but not everyone feels the same. If you prefer to stay in places with a more “you know what to expect experience”, you may want to pick stops with larger hotel chains.

You Will Need to Make Sacrifices Along the Way

Unless you have unlimited time, you will need to make some tough decisions about what to see and what you will have to skip. This applies to everything along the route — restaurants, motels, tourist attractions, old ruins, and alignments of the road itself. Around every corner there is more to see and at some point you will find yourself having to choose one thing at the expense of another.

We ran into this many times. Upon leaving Springfield, Illinois you are forced to choose between the older pre-1936 alignment of the road which runs through Girard and Nilwood or the newer alignment which runs close to the current path of Interstate 55. We opted for the older alignment but that meant we missed the Litchfield Museum and Route 66 Welcome Center.

We detoured from the old alignment across to Mount Olive to see the Soulsby Service Station but that detour meant we didn’t get a whole lot of time to check out the Chain of Rocks Bridge. We didn’t get to see the World’s Largest Catsup Bottle at all.

All of this occured in the first two days on the road and just in Illinois so it was a lesson we learned very early in the trip.

Be Flexible

Our first day on the road we tried to follow Jerry McClanahan’s EZ66 Guide down to the letter — I mean every single turn in every tiny town. After getting a little messed up when trying to visit the Two-Cell Jail in Gardner, Illinois we soon learned that it was OK if we missed a turn or two.

On the drive from Springfield, Illinois to Cuba, Missouri, we were running a bit late. It was getting dark so rather than following Jerry’s book through the maze that was St. Louis, we just let the GPS route us to Cuba as fast as possible. That meant we even — gasp! — hopped onto the Interstate for a bit. The good news for us was that we knew we were backtracking to St. Louis the next day so we would get a chance to re-drive that stretch of road on Route 66 proper.

Bonus tip: Get Jerry’s book. Seriously. Do it.

Give Yourself More Time in the East

The Route 66 sites on the eastern portion of the trip are very close together, as are the towns. This means the stops are more frequent and it is harder to cover any distance. You should factor this into building your schedule. You also need to consider you will be dealing with a lot of traffic until you get a ways out of Chicago. We did not and after the first two days on the road we were feeling a little burned out because we were spending more time on the road than expected. It was overwhelming and I was wondering how we would manage to keep up that pace for the full sixteen days.

Give Yourself More Time in Los Angeles

Once you reach San Bernadino, California you get into traffic. A lot of traffic. It may not look far on the map but it takes a long time to cover the distance. You will see some crazy drivers, crazy cyclists, and it will be a little stressful. Watch the final video of our Route 66 series and you’ll see how burnt out I was after that drive:

Enjoy the People Along the Way

You will encounter a wide range of people along the route. Some of them will be business owners and some will be fellow travelers. All of them have a story to tell so take the time to listen. From Rich Henry at the Rabbit Ranch in Staunton, Illinois through to Dan Rice on the Santa Monica Pier, you will come across some of the nicest people during your trip. We had great visits with Lowell Davis at Red Oak II, Tony at the Jack Rabbit Trading Post and Bob “Croc” Lile at his art gallery in Amarillo. Too many people to mention, actually.

We also saw many of the same people multiple times throughout our trip. We came to recognize their vehicles and even exchanged contact information with some of them. One of the best memories was sitting around the fire at the Blue Swallow Motel in Tucucari with the operators and a group of roadies listening to the tales from the trail. It was kind of sad that many of the group we had leap-frogged all the way from Illinois with disappeared in Texas and we didn’t see them again.

And, nothing will prepare you for meeting Harley in Erick, Oklahoma. 🙂

Route 66 Will Change You

It’s hard to describe, but after doing Route 66 I feel very different. Maybe it’s because it has been winter here at home but traveling around our local area doesn’t hold the same appeal as it did before. We saw so many iconic sites and attractions on our trip that it feels like everything pales in comparison. I expect we’ll get back to our old habits soon, but completing Route 66 feels like such an accomplishment that I don’t know what to do for an encore.

You Will Want to Do It Again

If we had unlimited time and funds, we would set off on Route 66 again without hesitation. I would even consider doing it “backwards” from California to Chicago, just to watch the landscape change in a different manner this time. From the arid desert to the Ozarks, it would be like watching the Earth come to life.

You will see so much that you want to see again or you will miss things that you want to go back and catch another time. You could do an entire trip just focused on abandoned buildings or a trip just working on natural attractions like Meteor Crater and Meramec Caverns. There is something for everyone and it could be a different trip each time.

Prepare to Be Surprised

Along the way you will encounter things that surprise you. For example, while exploring the Jericho Gap in Texas, we stopped at the old Jericho cemetery. We found they had a billboard with old photos of some of the people buried there and we spent a whole bunch of time looking at them, piecing together their family trees, and then looking to find where they were buried. This was something that wasn’t even on our radar yet it became a really interesting stop.

Just because you have seen many of these attractions online doesn’t take away the impact of seeing them in person. We still reacted like a couple of kids when we got to climb all over the Blue Whale of Catoosa.

Don’t be Afraid to Explore Off the Route

Many people will make a side-trip to Las Vegas as part of a Route 66 trip. Or give themselves a day at the Grand Canyon. While these are not exactly Route 66 attractions, they are close enough to make them viable for people who want to extend their trips. Route 66 serves as a great guide for seeing America, but don’t be a slave to the road.

Remember to Enjoy It

Don’t get caught up in your itinerary and focus on getting to the next designated stop. Don’t let temporary setbacks (like our dead battery in Holbrook) get you down. It’s all part of the experience. Don’t get caught into thinking of all the attractions as nothing more than a checklist to complete. Live the road, experience the life, meet the people. Remember to look up from your map long enough to take in the sights. For many people, this is a trip of a lifetime so enjoy it while it lasts.

Do It Now

There will never be a better time to do Route 66 than right now. While some new attractions come up like Pop’s in Arcadia, it is much more common to see attractions disappear. For every preservation success story like the Painted Desert Trading Post, there are probably a dozen or more stories like the Summit Inn where historic buildings are lost to fire or neglect. There will never be more Route 66 than what exists today so get out and see it as soon as you can.