The Great American Roadtrip: Los Angeles to Flagstaff.

Adventures in the American Southwest.

The idea of driving a long distance through the expanse of the American West has been especially intriguing to me for as long as I can remember. Growing up in the Midwest I never had an opportunity to see this beautiful part of the country, though this year I finally made the decision to get out and explore. Like the awe-inspiring lands of the West itself, the great American roadtrip has an alluring pull all its own. So for me, the prospect of a thousand mile drive in a brand new Cadillac across the high desert was an adventure which couldn’t be avoided any longer.

Over the course of this past year I’ve had a great opportunity to get well acquainted with Cadillac and the many smart people who are doing incredible things at one of America’s most iconic brands. I went to Austin with them to drive the 2016 ATS-V (a car that’s on my Christmas list), I spent time with the Cadillac crew in Monterey at Pebble Beach driving the CTS-V (shoutout to the Monterey Sheriff’s Office for being cool) and have had the privilege of spending a fair amount of time with the carmaker’s designers, engineers and marketers. In the past year I’ve watched as Cadillac has become a major champion for the menswear community through men’s fashion week and even its partnerships that support American designers. I’ve also come to better understand how much Cadillac believes in both the spirit of adventure (or being one to dare greatly as they say) and the significance of good design – two things that I have tried to instill into each trip I take and every page of this site.

Our trip was loosely organized around a few destinations: Flagstaff for Overland Expo (an interesting gathering of adventure-bound car and moto enthusiasts with a preference for “tactical kilts”; more to come on this event in a following post) and the sights around Monument Valley. I started out in Los Angeles where I was given the keys to a brand new 2015 Cadillac Escalade for the duration of the trip (comfort, V8 power and active fuel management for the win). I headed out of LAX straight across the desert to Las Vegas to pick up my cousin Wilson and crash for the night before heading to Flagstaff in the early morning the following day. The plan was to do a few days at Overland and then head North to the Arizona / Utah border and see all of the features of the Monument Valley – a place I have always wanted to see up close. Then we would head back to Las Vegas via Southern Utah and finally back to L.A.

In a short amount of time on the road we experienced nearly every climate condition. From the heat of the desert to a cold rain and an unseasonal little flourish of snow near Flagstaff. This being my first trip to Flagstaff, I was surprised by the look and feel of this part of Arizona. And I liked it, a lot. One night after a long day of driving we drank Barbera and ate woodfired pizza from the amazing spot Pizzicletta. While we only spent a few nights in Flagstaff and didn’t have the opportunity to try too many restaurants, that pizza place was utter perfection.

To see Monument Valley in all of its natural beauty was an incredible moment for me. Even though there’s a touristy thing going on there (and at the Forrest Gump spot on Highway 163 too) these are two sights that are definitely worth seeing at least once in your life. To just get out on the road is a pleasure in and of itself. I’d much rather be out there exploring (driving a Cadillac is a bonus) than doing almost anything else. It just makes you look at things in a different way. Travel has a beautiful way of helping you see things from another perspective and recalibrate. And for me, it’s always a great time to think deeply about things in a way I can never do in my daily life.

This trip was purely about exploration and discovery. I was the perfect mix of high and low that has served me so well in the past. It was about long drives on open roads, incredibly scenery, good wine, insane adventure mobiles and time to simply talk while the world moves by at 70 miles per hour.


The terrain in the High Desert of Arizona was interesting and not exactly what I had expected.




These vibes pretty accurately sum up Overland.
Please don’t ask me to parallel park this thing.


Red Wing Iron Rangers might not have been the best footwear choice for the wet and muddy conditions in Flagstaff.


We stopped at a service station and this was basically the view from the parking lot. The lands of Southern Utah are incredible.
Testing out some Vasque Sundowner GTX boots. They are awesome and were the perfect choice for this trip.


Every photo from Monument Valley seems fake.



Can’t help but to laugh at this. The Forrest Gump sign near the famous view between Monument Valley and Mexican Hat.
Monument Valley is as incredible as you would imagine it to be.


We weren’t in a huge rush, so we took our time to stop and explore whatever we found to be intriguing.



We crossed between Arizona and Utah several times throughout the drive.
We found a lot of little local markets to check out. This one in Arizona was on Native American lands.




Horses for sale at this roadside flea market.



Hmmm, 2711? Seems legit.






Comments on “The Great American Roadtrip: Los Angeles to Flagstaff.

    Reno Pete on November 24, 2015 8:08 PM:

    KC to LA some time ago. In an eldo touring coupe. Alone. From Denny’s to Denny’s. Grand Slams fueled me.Years in LA, then back. In a GMC 1-ton dually. Take that, gas bandits. Your photos are beautiful. I saw crazy-colored lurid skies like old Randolph Scott westerns. And a camel. I may have imagined that.

    General Gow on November 25, 2015 10:34 AM:

    All I could think when I got to the end was, “more, more.” I really need to hit the road. There is wisdom in the air out there. Just need to breathe it in. My vehicle of choice would be about 60 years older, but I understand the appeal of the obvious comfort of that Caddy too.

    Brad Steward on December 1, 2015 12:31 AM:

    Would have loved to have seen Caravan Outpost’s version of this trip. Love their other Cadillac projects.

    andrewthompson86 on December 9, 2015 8:43 PM:

    Just did LA to Cave Creek, AZ back at the end of October in an Escalade. Heck of a comfortable way to travel the open road.

    Andy on December 10, 2015 10:02 AM:

    Next time bring me along.

Comments are closed.