Kicking off 2026 with a Goliath Post in tribute to how I spent the first two weeks of the year. Buckle up, my dudes!

Three months ago, the CEO of the non-profit I work for called me into his office and asked me what I was doing for the first two weeks of January. We weren’t even seated for the question, so it seemed inherently casual. He wanted to know – if I didn’t have any plans, that is – would I  be interested in driving from Santa Monica to Chicago, then on to Detroit, following along historic Route 66 as part of a vintage nine-car caravan?

Full disclosure: sure, I work for an organization wholly inspired by the automobile, but my appreciation for vehicles of any kind is not natural and was borne entirely of seeing Aaron’s interest in these things firsthand. Truthfully, I would likely never have gone for this job if not for Aaron. So while I am always keen for an adventure, when presented with the option to go on this road trip, I was apprehensive. Twelve days is a long time to spend on the road with people that are not friends or family. It’s a long time to drive a car that’s twice as old as I am, to be “on the job”. An adventure, sure. But whoof, a lot of me wondered, at what cost? Am I really enough of a car person to do this?

I didn’t know the real answer to that question, and in the end it was not my sense of adventure or faith in my ability to fake my car-ness for nearly two weeks straight that made me say yes. It was, I am afraid to say, simply my natural response, ingrained in my emotional muscles from years of being a yes-person. (I’m not proud of it and I’m still working on it! These things take time.) After a week or so of talking to Aaron about it and considering my options, I said yes, and signed up.  

The Drive Home, the name of this little annual adventure, is a seven-year old partnership between our organization, America’s Automotive Trust, and the Detroit Auto Show. Each year a new drive is planned, always in vintage cars, and always ending at the first day of the show in Detroit. The Drive celebrates the significance of cars in American culture, the importance of not just vintage cars, but maintaining them and keeping them on the road when you can, and really, just the sense of adventure that comes hand-in-hand (or hand-on-wheel) as part of a road trip. In an irresistible turn of timing, 2026 marks the centennial one of America’s most iconic roads: Route 66. There was no question what route this year’s Drive would take – we would be on the Mother Road. 

On the overcast morning of January 3^rd, when we took off from the iconic Santa Monica Pier and headed towards our first stop at the Historic Rancho Cucamonga Fueling Station, I realized I knew nothing about Route 66. I had seen Cars. That’s about it. To fill in the gaps in my knowledge, I imagined that the route was abandoned because it was less efficient and lacked the lanes of the new interstate system, but I still pictured it as a fairly direct highway, kicking off in Santa Monica before following a relatively straight line all the way to Chicago.

Friends, I was so wrong.

For those as unknowing as me circa three weeks ago: all Route 66 did was connect a bunch of preexisting town-to-town roads. It’s called the Main Street of America because it IS Main Street for many of its long miles. If you drive any significant stretch of Route 66, you will at many points find yourself on beautiful, historic, sometimes abandoned, sometimes restored and thriving, actual Main Streets of towns in countryside you’d never be able to point out on a map. So many of these towns are still filled with people passionate for the route, passionate for what it meant for Americans when it was first opened. Some of them were born and raised in these places; even more fell in love with the route on their own road trip, picked up their lives, and relocated to Tucumcari, New Mexico; to  Adrian, Texas; to Miami, Oklahoma. You can tell the moment you meet these people that nothing sparks their joy like being a part of Route 66, of preserving it for future generations. There was not a single town we stopped in where this was not my experience.

It was, in the end, an eleven day road trip, inherently impossible to catalogue effectively in a single post. So, obviously, I did it across eleven different posts on Instagram.

I continue to hope I will ween myself off of Instagram entirely one day, so in that vein, I’m going to pop everything I put there up on here to make sure my memories don’t disappear suddenly because Instagram unexpectedly dies a death.

Day 1: Santa Monica to Barstow 🌴>🏜️

Highlights: Getting to park on Santa Monica pier, the most delicious breakfast & cutest hat from the Mel’s Diner at the endpoint of Route 66, visiting Rancho Cucamonga historic service station and getting an even CUTER hat from said service station, first time wigwam motel experience (just driving through), and finishing off with an A+ dinner at Roy’s Cafe in Barstow.

Day 2: Barstow, CA to Kingman, AZ 🏜️>👑

Highlights: First big stretch of Route 66, seeing bush planes taxi at Roy’s Cafe in Amboy, feeding a delightful burro in Oatman, seeing the sun break through the clouds on the Sitgreaves Pass, taking Woody (the ‘65 Country Squire I’m driving) on many twists & turns, a photo op in Cool Springs, and a five-star desert sunset in Kingman.

Day 3: Kingman, AZ to Winslow, AZ 👑 > 🎶

Highlights: Everything about the Kingman Visitor’s Center, blue blue skies and all the floofy desert clouds, ghost gas stations galore, the recently restored Osterman Gas Station & the warm welcome we received, not almost running out of gas, remembering to not call Winslow Arizona Winston Arizona, Flagstaff!!, lots of laughing, and being a lot less exhausted than I was this time yesterday.

Day 4: Winslow, AZ to Albuquerque, NM 🎶 > 🌵

Highlights: Red Rock Park, the amazing people in Gallup, NM that welcomed us at the El Rancho Hotel, lots of high desert driving, and rolling up to Albuquerque where we got a private tour of the most amazing neon sign collection I’ve ever seen in person.

Tomorrow marks the halfway point! Maybe I will find a new pose? But probably not 🤣

Day 5: Albuquerque, NM to Amarillo, TX 🌵 > 👢

Highlights: Turning a loss (major toe stub first thing in the morning) into a win (spontaneous cozy moccasin purchase at Cline’s Corner), falling in love with the flag of New Mexico and also the gem that is The Blue Swallow Motel, meeting more excellent humans, meeting Izzy the Cat at the Route 66 Midway Point, more neon, and experiencing the beautifully cornball roadside attraction that is The Big Texan Steak Ranch. They do NOT brag enough about their lemon cake.

Day 6: Amarillo, TX to Weatherford, OK 👢 > 🛠️

Highlights: The best swag bag from Visit Amarillo, a lovely hotel stay, breakfast tacos, getting to answer emails during daylight hours for the first time since last Wednesday because we got stuck while the 1965 Ford Country Squire got fixed, and finally making it to Weatherford sans any planned stops to catch up with the rest of the crew at 7pm.

Day 7: Weatherford, OK to Tulsa, OK 🛠️ > 🛤️

Highlights: Driving the biggest uninterrupted stretch of Route 66 so far (a truly wonderful experience with blue winter skies), Pops on 66 and their A+ modern building and swag, meeting Ed Threatt Sr. at Threatt Filling Station, getting to see the cutest shop in Tulsa that generously worked on several of our caravan cars (@atlasautomotive_route66), & being back in the Squire. One of my favorite days of the trip!

Day 8: Tulsa, OK to Lebanon, MO 🛤️ > 🌾

Highlights: Our brief stop at the gem that is the Coleman Theater of Miami (Mia-muh), OK, meeting the locals at Main Street Cafe, seeing the original inspo for Mater in Galena, KS, driving into Lebanon (Leb’nun), MO at sunset, being greeted by a huge crowd that joined us for a Route 66 Museum tour, and eating the best mustard BBQ sauce I have ever had at Smokin’ Joe’s of Wrinks Market, in the company of excellent car and motorcycle people, where I learned the term “cycle [sickle] bum”. Would 100% Leb’nun again.

Day 9: Lebanon, MO to Springfield, IL 🌾 > 🎩

Highlights: Yet another blue skied winter day spent driving old stretches of Route 66, the warm welcome from the team in Rolla, MO (including a cat!!), seeing the Gateway Arch for the first time, driving across Bridge of Rocks in the Squire, lunching (fried cheese curds!!) at Weezy’s on 66 (complete with some of the shortest bathroom stalls I’ve seen), a wheat field sunset for the ages, and excellent company in the coolest repurposed building in Springfield, IL at Motorheads Bar & Grill.

Seeing firsthand why Route 66 is called America’s Main Street continues to be one of the best parts of this trip. Today we finish in Chicago, and tomorrow we cannonball to Detroit to help open the Detroit Auto Show. It’s been a helluva ten days!

Day 10: Springfield, IL to Chicago, IL 🎩 > 🏙️

Highlights: Seeing Mama Burger at the Museum of Giants in Atlanta, IL, the first snow !! (just a smidge of it and already on the ground), checking out the Pontiac Museum, and hitting the final stretch of 66 – which was not pretty 🤣 but still an achievement – and getting a photo at the official sign.

Big Bertha tribute post: (written from the cozy comfort of a 2026 Expedition, because the Squire is now in the trailer for the rest of this journey 🤣)

I logged just over 2,000 miles in this car in the past ten days, and it was SUCH a trip. Sure, it would’ve been nice to have had a car whose transmission didn’t quit 35 miles outside of Chicago, but she gave all she had to give and we had SO many laughs across 9 states. Born in 1965 and still going (ish), thanks for the journey big girl!

Day 11: Chicago, IL to Detroit, MI 🏙️ > 🚘

(For the record, I write this from the comfort of my own bed, having slept for 17 of the last 24 hours.)

Highlights: THE most beautiful sunrise, only having a minor menty B at a Starbucks in Michigan City, and finally, after 2,300+ miles, making it to Detroit.

BB, this beautiful 1965 Ford Country Squire, kicked the can due to a slipping transmission 35 miles outside of Chicago. With the help of a trailer, we were able to at least get her dropped off at the Detroit Auto Show. And as she sat there outside the building, with no one in particular super eager to drive her in her slippery state, it became clear that there was only one person that should take her through the convention center doors in the relative safety of her low gear. (It was me.)

Thanks to everyone who followed along on this very long but also incredibly fast adventure. I know that some genuinely terrible shit has been happening in this country and in the world while I’ve been on this road trip, and at times I almost held off posting because it felt comparatively vacuous and silly to share a giant soda bottle in Arcadia, OK or another picture of the sky. But I will tell you – whether it was the kindness of total strangers, the truly vast and varied landscapes, or moments like catching an anti-facist protest in towns where you least expected it – this was a reminder that there are good people and beautiful things here. And it’s not that I didn’t know that, or that it means you don’t have to do anything to try and fight against what’s happening. Nothing gets done in something a simple as an Instagram caption. But that was my main takeaway from this (albeit exhausting) escape from my regular life. America may be a dumpster fire, but it is so worth trying to save – and more people than you think in places you would not guess feel that way too.