One Year Later – Reflections On My Route 66 Adventure

Route 66 Oklahoma

I don’t normally recognize trip anniversaries, otherwise that’s all I’d be doing. Every now and then though a trip is so remarkable and so impactful that it becomes part of who I am. This is rare but, when it does happen, it is exceptional and driving the entirety of Route 66 was one such adventure. It’s hard to believe that a year has already gone by; it seems just like yesterday when we got up early, left Chicago and nervously started to bump along the Mother Road. What ensued was a fun and enlightening two-week trip west, marked by quirky people, gorgeous landscapes and a lot of pie. Today I want to share what Route 66 has meant to me in those intervening months and why, more than anything, it’s so much more than just an interesting road trip. (I recently produced a podcast all about Route 66, which you can listen to here.)

Once again, a VERY special thanks to Marriott International for sponsoring this great adventure. Every night we spent the night in a different Marriott International brand hotel and without them, would not have been able to realize this dream.


I’ve already written a lot about what I discovered as I drove the 2,400 miles from Chicago to Santa Monica, California and it’s not my intention to simply regurgitate everything here. Well, not completely at least. It’s hard for me to say exactly why I wanted to tackle the drive in the first place. It had been something I wanted to do for a very long time, but it wasn’t until I visited a museum exhibition about the route that planning started in earnest. I spent about a year mapping and researching Route 66, preparing to make the most of the drive. What motivated me was a strong urge, a yearning to get out there and be an explorer again. Not to depend on others and instead get along on my own wits, exploring the heart of America at the same time. While I spent hours researching the important stops along the way, it wasn’t until I started driving the Mother Road that I truly understood its importance.

Amarillo Texas

Sure, Route 66 transects the country, exposes drivers to all sorts of new places and people, including those quirky stops that have become the stuff of legend. But, unlike most other trips, Route 66 isn’t at all about those stops, it’s about the drive itself. In this instance, getting there IS the adventure. It’s about tracing the footsteps of travelers before us, hoping to catch a glimpse of their American view, at least in part to rediscover one’s love for the country. That was the unintended consequence for me. In an age when many of us are upset by the daily machinations of politicians, it was important for me to get out into the nation and to see for myself that it is still indeed a great country. I was also reminded of an important travel truth, that most people everywhere around the world are good hearted and kind, and that’s especially true here in the U.S.

Route 66 Missouri Gary's Gay Parita

Not once during those two weeks did I have a negative encounter. On the contrary, every day brought new and positive people into my life, eager to share their corner of the country with me. That’s remarkable, that’s special and that’s rare in the travel experience and yet, along Route 66 it’s just normal every day life. Maybe I’m being a little too philosophical in my recollections of the drive; maybe I’m willfully ignoring those hiccups along the way. But, in all honesty, there weren’t many. Few wrong turns were made, everyone was hospitable and other than lamenting the fact that a few kitschy landmarks along the way weren’t open, the experience was just as positive and affirming as I had hoped it would be.

Route 66 California

By the time we battled Southern California traffic to end our day and drive on the beautiful Santa Monica pier, I was nearly in tears. It was a cathartic moment, but also an abrupt one. I had become very used to my daily routine on the road, of navigating the byways of America and keeping my eyes open for the new and bizarre. I had also become used to seeing the country as it is and not as people imagine. I enjoyed those small towns dotted around the landscape and improbably located boutiques and restaurants. When I once again was reintegrated to the coastal bubble and sprawl of suburbia with its PetSmarts, Targets and Panera Breads, I was in shock. It all seemed so incredibly fake and pointless to me. What were the people there doing? Didn’t they know what was just a few hours away and why weren’t they all heading inland to discover it for themselves. Instead, they were plodding about doing their errands around a seemingly endless number of Town Centers and strip malls. It was depressing and I instantly felt superior to them. I felt as if I had been allowed in to see the sanctum sanctorum of the country and those secrets had somehow transformed me. I knew right away that I wasn’t the same person who started the drive in Chicago, but I didn’t know what to do with that knowledge.


In the months that have since intervened, I have come off of that pompous high horse. I realize that no, I’m not superior to those suburbanites because, ultimately, I’m one of them. I think it was that sudden realization that brought about my flash of anger. After having spent so much time in improbable spots around the country, I enjoyed being different, visiting really out of the way places and not being just another tourist somewhere. It’s this individualism that I think defines Route 66 and ultimately has led to its place in our collective hearts. Route 66 is unique in that it is an adventure that allows us to be anyone we want to be, no matter our backgrounds. It’s a trip of adventure and self-reliance, but also of anonymity and reinvention. It’s a remarkable experience and an intensely unusual one, at least in my opinion, and that more than anything else is what has me yearning to return.

It’s not the drive per se that I’m desperate to do again, but it’s for the opportunity to recapture how I felt during the process that has me so motivated. I think that’s probably the case for anyone who tackles the entire drive. It’s not the quirky stops or greasy diners that has them wanting to go back, it’s for the totality of the experience.

Wow, so this was a little deeper than I had intended, but that’s the nature of the Mother Road. It elicits unusual and complex feelings in those who have driven it, and it’s that strange codependent relationship that makes it so very special.

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.

1 thought on “One Year Later – Reflections On My Route 66 Adventure”

  1. I share your vision of Route 66. I have traveled the Mother road 3 times. First in 1955 from Pryor, Ok. To Santa Monica with my husband & 4 year old daughter. Then after retirement in 2012 alone. Third time in 2018 with a group. Loved every minute. It is a fabulous trip to see the real America

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