Route 66: Why I Went, What I Learned and What’s Next

Route 66 Matt Illinois

Every day the sticker stared at me. To be more accurate though, it’s a postcard that I taped to the lamp next to my desk. A simple black and white postcard, all it says is “US Route 66.” It was more than that to me though, it was a daily reminder, a prod that while never insistent, was always there, hovering at the edges. It was my reminder of a trip I’d always wanted to take, I just never seemed to be able to make the time for it. Of course that’s what I told myself, the truth is, I think I was putting it off. More on that in a bit, first I want to share why I decided to drive the entirety of the true Route 66 from Grant Park in Chicago to the Pier in Santa Monica and what the adventure has meant to me.

Two summers ago on a warm day in St. Louis, I found myself meandering through the halls of the Missouri State History Museum. I didn’t have high expectations, but I quickly realized how wrong I was when I discovered a fun, engaging and modern museum sharing any number of stories from the state’s past. One of those storylines was featured in a special exhibit, Route 66 as it runs through Missouri. I’ve always been fascinated by Route 66 and I can’t exactly tell you why. Maybe it’s the same feeling of nostalgia that seems to afflict so many of us around the world, or maybe it was something else, something deeper. Whatever the reason, that longing, that fervent desire to see the country along this now-defunct road system was a part of me I could no longer ignore.

I approached Marriott International with my concept for a few different reasons. I’ve always had a great respect for the company (they were the first hotel with which I collected hotel points), they have a great American story just like Route 66 and somewhat amazingly, I discovered that I could travel across the country and stay with a different brand every day. Since their merger with SPG, they now have scores of brands from the Fairfield Inn to the St. Regis and everything in between and I knew that a hospitality company was the ideal fit for the Route 66 adventure. Kindness and hospitality is actually an important aspect of the drive itself, something I learned on the very first day of traveling.

Driving with photographer and videographer extraordinaire Brendan Van Son, our first stop in Joliet, Illinois actually set the tone for the two weeks that would follow, although I certainly didn’t know it at the time. Joliet has done a great job embracing its history, especially Route 66, a fact that is made clear as soon as you drive into town. Signs, plaques, special road markers and even a museum are all in town, the perfect first stop for any would-be Route 66 expeditioner. While not every locality or even state so thoroughly embraces the Mother Road, every day we saw something, some reminder, whether it was a road sign or a campy neon emblazoned motel by the side of the road. More than the kitsch though, it was a chance encounter in Joliet that was the truly important event. That’s because we weren’t the only people in the Route 66 museum, others were there including a retired couple from Ottawa, starting their own bucket list drive. They planned on spending the summer driving the Route, once finished they then wanted to tackle the Pacific Coast Highway before finding their way back home. That was a common theme throughout my own Route 66 adventure, most of the through-drivers I met weren’t American, they were from places like Canada, Germany and even New Zealand.

I thought about that international presence for a long time before finally deciding that we all had the same goal, the same quest. We wanted to discover (or rediscover) the real America; an unvarnished look at the best we have to offer. Although in my youth I lived in places like Missouri and Kentucky, I’ve been an East Coast elite liberal living in a carefully constructed bubble for nearly 20 years. In that time I’ve forgotten what makes the country so great, and I knew that. That was one of many goals I had for myself before the drive, I wanted to assess the state of the union in 2018 away from talking heads and pundits. And for the most part, I found what I was looking for. Sadly even just a couple of weeks later, the day-to-day experiences are somewhat of a blur, but every day I was surprised by what we discovered. From small towns that probably shouldn’t exist to some of tbe nicest people I’ve ever met, each leg brought new stories.

I finally gained an appreciation not only for the massive size of the country, but just how diverse it is. Within a week I went from the woodsy trails of the Ozarks to the hot and dusty deserts of the Southwest. I met pie-makers, Native Americans, purveyors of fireworks, retirees and everyone else you can imagine. Every one of them was fiercely proud of where they live and together, they helped create an incredible mosaic of what America in 2018 is really like. The truth is, it’s not that different from years past. I didn’t find seething anger, I didn’t find intolerance and I didn’t find a willful ignorance of facts. No, instead I met happy, proud and engaging people, all eager to share their lives and stories with me. You don’t see that on the news.


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 a deep 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’s going to take me a little while to get over that frankly. 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. I’ll soon move from being sad to being joyful at the lessons learned from the journey and how it marked an important turning point in my life. Of course, none of that is known to me today. No, instead I’m just organizing my photos, putting away the trinkets I picked up and planning my next trip. It won’t be for months or years that I truly appreciate the effects driving across America had on me, and that’s fine. In the meantime I have the wonderful memories to keep me content as I try to wrap my brain around ways to share individual moments from the drive with you all and to, hopefully, encourage you to undertake your own quest, to seek your own grail and to discover more not about a place but about yourself.

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 “Route 66: Why I Went, What I Learned and What’s Next”

  1. Matthew Pichon

    During a 2003 trip through Illinois, I observed many remnants of the old highway along side of Interstate 55 heading northward toward Joliet. Too bad there was no way to take photos.

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