Reflections on Driving Route 66


Every morning I sit down at my desk, bring my computer back to life and prepare to drink dangerous amounts of coffee. Before all that though, I look over at a simple postcard I have taped to the wall – “Route US 66.” That’s all it says and it’s been hanging there for years; the only travel related item I have hanging around my desk. For a long time it served as my motivating factor to make driving the entirety of Route 66 a reality, which I did earlier this year. Now that I’ve completed my quest, it serves a much different purpose. It’s there to help me remember the amazing experiences along America’s Main Street, but it’s also a source of inspiration to keep dreaming and keep planning epic adventures. As the end of the year draws to a close, I want to spend some time reflecting on my drive across America, what I discovered, what I learned and what it means in the broader context of my life.

Grand Canyon Arizona

Shock and Awe

I’m fairly certain I amused my driving partner, acclaimed photographer Brendan Van Son, every day of the drive as I experienced true surprise around every corner. I didn’t exactly know what to expect before the drive, that was one of the most exciting aspects, but the level of education I experienced was nothing short of extraordinary. Leaving Chicago, mentally I prepared myself for endless farms and prairies until we hit the Southwest. But almost everyday we witnessed incredible changes in the landscapes that, yes, did include a lot of wide-open spaces, but so much more than that. Missouri is probably what surprised me the most, a lot of Route 66 through the state includes the Ozarks, complete with dense forests and rivers running through them. In fact, those gorgeous landscapes changed so often that they unexpectedly added a lot to the adventure. It was my first time in many of those spots, from Kansas to New Mexico and beyond and I was shocked at how off my preconceptions were. It forced me to rethink everything I thought I knew about my country and, in the process, to appreciate it that much more.

Carthage Missouri

The people also made a strong impact on me and I met amazing individuals every day on Route 66. Before the drive I knew I would enjoy my time in places like Chicago and St. Louis, but what I didn’t expect was to love many of the smaller towns along the way. In Springfield, Missouri I found a wonderfully quirky city that revels in kitsch, whether it knows it or not. In Carthage, Missouri I was dumbfounded to find one of the most beautiful town halls I’ve ever seen and in Las Vegas, New Mexico I discovered a quirky arts community I certainly never expected. Just as the landscapes opened my eyes, so did these towns and cities. Each one was full of people who had lived there for their entire lives and, most importantly, enjoyed living there. They are proud and fiercely eager to share what makes their communities so special with outsiders and for that I am grateful.

Texola Oklahoma

Not as Difficult as I Thought

Let me preface this by adding the caveat that navigating the true Route 66 is a challenge and does require a couple of people in the car. Spanning eight states and more than 2,300 miles, US Route 66 was created in 1926 from an existing network of trails and roads, most of which were very primitive by modern standards. Over the years and several realignments, the roads that comprised the route were modernized, widened and paved making it easier for people to travel and experience the country. After the introduction of the Interstate Highway, Route 66 began a slow decline as communities were bypassed by the new super roads. This eventually led to its decertification in the 1980s when US Route 66 officially disappeared. Of course Route 66 hasn’t completely disappeared, it exists from Chicago to Santa Monica through alternate routes, frontage roads, gravel trails and a variety of other means. Since Route 66 doesn’t officially exist anymore, to ensure you stay on the old road takes constant adjustments, turns and realignments. But that’s not really what I mean by difficult. The idea of driving across the country sounds daunting and tiring, but spreading it out over nearly two weeks ensured we could manage the drive without forcing ourselves into an early grave. In an ideal world, the drive should take even longer, which means shorter daily legs and more opportunities to stop and explore, which is what Route 66 is really all about anyway.


Curiosity is Everything

I love travel for many reasons, but at the core is my deep longing for the spirit of discovery that a only great trip can provide. I haven’t had enough of that lately and Route 66 demonstrated to me just how important it is to be well and truly excited while traveling. More than rediscover my own country, I think I learned a lot about myself in the process. I spent years planning this trip and the journey itself was much more demanding than I had thought. This isn’t the same thing as driving across the country on a highway. No, Route 66 in 2018 exists as a patchwork of roads, dirt, country and interstate, all woven together through time and history. Some parts of the Mother Road no longer exist and others may be enjoying their last days on the planet. To drive the true Route 66 is hard and takes constant attention to the thousands of turns and curves from Illinois to California. It’s that level of concentration though that I think made the journey as special as it was. Forced to concentrate, forced to watch, it’s a style of driving or riding as a passenger few of us enjoy anymore. There was no voice emanating from my phone telling me which way to go, instead Brendan and I had to figure that out for ourselves. (With a lot of help from guidebooks.) Most people don’t drive like that anymore and I was shocked at the benefits it can have. Sure, the journey took a lot longer than driving the highway, but that’s the point. My adventure on Route 66 wasn’t about a single destination, instead the trip was all about the journey. That’s unusual if not totally unique nowadays.

Writing this I feel an aching sadness, but not one born from melancholy. No, it’s not a tearful sadness, but more of the sort when you miss a dear friend. The Mother Road filled a gap in my soul I didn’t know needed filling, it was a companion I didn’t know I was missing. I’m sad that I’m no longer on the road, rolling across America and it has taken me a little longer to get over that than I thought. But this is as it should be. Important life experiences should be discrete, they should be limited and they certainly can’t be repeated or reproduced. Although it’s been many months since I ended the drive, I know that I will continue to learn from the experience, to grow and I hope to share those lessons here. At the end of the day, this adventure was about encouraging others to undertake their own quest, to seek their own grail and to discover more not a about a place, but about themselves.

By: Matt Long

Matt has a true passion for travel. As someone who has a bad case of the travel bug, Matt travels the world in order to share tips on where to go, what to see and how to experience the best the world has to offer.

5 thoughts on “Reflections on Driving Route 66”

  1. I was not be able to traverse Route 66 but I did found a similar appreciation of the US by taking the train – specifically Amtrak’s Southwest Chief from Chicago to LA with many stops in between. As an international college student back then, that journey helped expand my horizon and gain a deeper understanding of the American heartland away from the two coastal metropolis.

  2. Drove the entire road in 2004. In a red Corvette convertible. Shipped my vette to LA, flew there from Florida and drove the road from LA to Chicago. We spent 14 days driving it. You’re right, it would be great to spend 6-8 weeks driving it. After ending drive, drove from Chicago to home in Cocoa, Fl. Along the way, stopped in Bowling Green, KY to visit the Corvette plant. Also drove about 400 miles of road in 2016. Would love to drive its entirety every year but can’t seem to fit it in that often. :-) Loved your article and pics. You describe the experience perfectly.


    Oi Matt, legal seu post, boas reflexões para pensarmos em nossas vidas. Para a maioria dos brasileiros não é fácil viajar para os EUA porque a diferença de moeda é grande, nós devemos multiplicar por 4 (1 USD = 4 R $).
    Eu fui para 66 no ano passado mais especificamente para Kingman e no próximo mês de maio eu vou para Barstow e San Bernardino, parte da minha viagem LA para LV.
    e se você precisar de alguma coisa aqui no Brasil não hesite em entrar em contato comigo, desculpe pelo meu inglês …. rsrs.
    Hi Matt, nice your post, good reflections for us to thinking in our lives. For most part of brazilians its not easy to travel to USA because the difference of currency its big, we have to multiple by 4 ( 1 USD = 4 R$ ).
    I went to 66 last year more specifically to Kingman and next May i go to Barstow and San Bernardino, part of my trip LA to LV.

    Best Regards e if you need something here in Brazil don’t hesitate in contact me, finnaly apologize my english….rsrs.

  4. Hi Matt,
    When we left Chicago we allowed 4 weeks to make it to LA. In 4 weeks we made it to Falgstaff, As. There is so much to do, to see and people to listen to as they tell stories about Route 66. Each town was unique. Museums, car shows, cafes and much more was available. We went back the next year and finished the LA to Flagstaff portion of 66. This is such a great way to see and experience America. I would like to do it again as I know there is a lot more to see and do.

Comments are closed.

I help you experience the best the world has to offer!

Please enter a valid email address.
Something went wrong. Please check your entries and try again.