Route 66, a few kicks, cadillacs, wigwams and a good corner to stand on.

When Megan and I set off across the country, we had a little list of things we wanted to see and a rough guess of where we’d be staying each night. We had a tight timeline, but we were pretty determined to still see some crazy awesome things because America is big and there’s a lot to see and driving across the country is a pretty big fucking deal.

I’ve always wanted to drive part of Route 66, or at least see some of the strange and kitschy things along the route, and our route, from Richmond to Palm Springs, had us on I-40, which parallels Route 66 for a long, long while. And so, we managed to throw in some Route 66 sightseeing, all of which was totally serendipitous, which is usually how some of the best adventures are had.

Cadillac Ranch.DSC_8842

So we were somewhere between here and Texas and we finally realized that we were driving right next to Route 66, and I was all, where the shit is that place with the cars in the ground where you can spray paint them and shit? And then we google it – fuck yes, google – and learned that the Cadillac Ranch, that place with the cadillacs painted and stuck in the dirt, is in Amarillo, Texas, a place we’d be driving right through and so we went. After getting Whataburger, of course, because hamburgers.



It was a quick stop. We maybe spent 20 minutes there and some of that time was spent cursing at Megan’s dog Chance, who insisted on pissing on each and every cadillac. We didn’t have any spray paint, so we didn’t leave our mark on the cars, but it was really fucking cool, nonetheless. It’s such a weird site, these cars stuck ass-end in the middle of this desert field in Texas.


Wigwam Motel.

I woke up early in Oklahoma City. I should have gone for a run, but instead I started googling the top sites to see along Route 66 and the Wigwam Motel came up. It was on all the lists. There used to be seven of them or some shit, but now there’s only two and, like fate, one of them was along our route, in Holbrook, Arizona.


You’ve got to call to make a reservation at the Wigman Motel and the office opens at 4pm, so we didn’t know until we were a few hours out if we could stay there, or, really, if the place was even still open, but, me driving and Megan calling, we found ourselves a room, a cheap room, at that, and dog friendly too.


This place is classic Route 66. We felt like we could go to sleep there, in our wigwam, with classic cars parked in front of each and every wigwam (this place inspired the Cars movie), and wake up in 1967. The whole town has this feel of nostalgia, of times gone and it holds a certain sort of magic that I’ll never forget. It was here, in Holbrook, at the Wigwam Motel, that we started drafting our movie script, something like Hot Tub Time Machine, except different and probably better because ROUTE 66, Y’ALL!



UPLOAD - 15 FEB - Rt1

We drove around the next morning, just through this little town, and it’s all Route 66 kitsch. It’s rock shops and steakhouses with giant carriages on the roof and it’s magic, mostly, this little town along this forgotten route.

UPLOAD - 15 FEB - Rt2

Winslow, Arizona.

We went to a Mexican place for dinner the night we were in Holbrook, since the diner across the street from it was closed. We had two beers each, got a little high off the altitude and a day spent driving in from Oklahoma City, and we were loud and silly and probably totally annoying to the other customers in the place. This older gentleman, sitting across the restaurant from us, started up a conversation, asking us where we were from, where we were going, what jobs we had and the usual smalltalk. He gave us some tips for seeing the Grand Canyon, which we didn’t take, but should have, and then, just as he and his partner where about to leave, he comes over and says, if you’re going toward the Grand Canyon, about 30 miles away there’s a place calling Winslow, Arizona.

We were like, oh, ok, that sounds lovely.

And then he says, there’s this park where you can stand on a corner in Winslow, Arizona, and then, right in the middle of this little Mexican place, I started singing the Eagles song, “Take it Easy.” And really, by singing I mostly mean screaming because if you’ve ever heard me sing, my singing is pretty much synonymous with screaming,

Well, I’m a standing on a corner
in Winslow, Arizona
and such a fine sight to see
It’s a girl, my Lord, in a flatbed
Ford slowin’ down to take a look at me


We downloaded “Take it Easy” on the five minute drive back to the hotel and then sang it approximately 4,559 times over the remaining miles from there to Palm Springs. In fact, there was a whole multi-hour block of time when we were only listening to the Eagles, especially after we hand the chance to stand on a corner in Winslow, Arizona.


No shit – there’s even a flatbed Ford parked out in front of this Route 66 corner.

Someday I’d love to drive as much of Route 66 as still exists, because it’s fading fast. The towns used to live on the traffic the Route brought, but the interstate has replaced it, leaving it broken in a lot of places and leaving those little towns with not much else but broken down kitsch. It’s a neat thing, Route 66, and the towns along the way, even if they’re not what they used to be, they still have this almost eerie sort of nostalgic feel that made us both want to step back in time, if only for a bit, and experience Route 66 in all of it’s magical glory.

7 thoughts on “Route 66, a few kicks, cadillacs, wigwams and a good corner to stand on.

  1. These photos are amazing, and seriously ever since your trip I’ve talked to Matt about how much I want to go to this Wigwam motel, ha. Seriously, so glad you had such a great time and man I want to go on another road trip soon.

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