With 2026 around the corner, you may be thinking about taking the opportunity to celebrate Route 66 on its 100th anniversary. I recently made the entire trip, from Chicago to Santa Monica, all 2,448 miles of her, through 8 states and 3 time zones and I would do the trip differently now, knowing what I know now. So perhaps I can help you with your Route 66 planning.

Let’s begin by telling you that I have the answer to the big question everyone has asked me, over and over again. “What’s the one thing you saw on RT 66, the one highlight, the most memorable reason that I should jump in the car and take the road trip.” (You’ll have to watch the PhotowalksTV video for my answer! Timestamp: 11:00.)

But first remember that visiting the entirety of Route 66 is important because it was America’s first highway, created as a way to bring business to the many small town merchants who were being overlooked. Cut to the 1950s, and a presidential decision to create super highways, eventually leaving Rt. 66 in the dust. But it’s still there and ready for your business. Want to get your kicks by seeing the America of Elvis, Marilyn, shakes, bowling alleys, old western towns and such? It’s still alive on Rt. 66, if you know where to look.

Now, how do you want to do it?

The sign on the Santa Monica Pier clearly states that it’s the end of the road. So if you live in California, as we do, do you just start here, and work your way to Chicago? Or do you do as I did, fly to Chicago, rent a car and take the drive the way Nat King Cole intended?

The trip after all is immortalized as one that is all about “motoring west.”

This is how most people do it, and the one I would recommend. You get to see the landscape change in a way that’s just so dramatic. Farms and prairies to the red rocks of the southwest, getting redder and redder along the way. 

Something else you really need to know that people don’t tend to tell you: Route 66 still exists, but not completely. Portions of Route 66 is like it used to be back in the 1950s. Others have disappeared. Your navigation system doesn’t know anything about Rt. 66 and will do everything possible not to let you ride it, but instead throw you onto the highway.

To get around this, there are apps and books. The book of choice is “EZ66 Guide for Travelers” by Jerry McClanahan and it’s considered the gold standard because it has turn by turn directions for each direction.

How much time to allot to the trip?

We did three weeks, which is more time than most people can devote tp. My number one regret was that three weeks wasn’t enough. I wish we had taken five weeks, which again, I know is unrealistic for most people. But at three weeks, you’re still going to miss a lot, I know I did. I figure I saw about 60% of what I would have wanted to catch. 

So what to do? Don’t do it in 1 week–that’s just too crazy. But I’m going to map out a 2 week itinerary and a 3 week one for you. Stay tuned for those. We’ll get to them as well.

I have the highlights for each state in the video (please watch!), but meanwhile, back to your itinerary. I recommend you pick and choose, because you can’t see it all, unless you were willing to devote 5 or 6 weeks.

Two week Itinerary

The minimum is two weeks, and here’s what I would do:

1. Chicago to Springfield, ILL 3 hours (Pontiac and Atlanta)
2. Springfield to Rollo, MO 3 hours
3. Rolla to Springfield, MO 2 hours
4. Springfield to Tulsa 3 hours (Includes stops in Galena.)
5. Tulsa to OK City 2 hours (Includes stop in Stroud)
6. OK City to Shamrock, 2.5 hours
7. Shamrock to Amarillo 90 minutes
8. Amarillo to Tucumcari 90 minutes
9. Tucumcari to ABQ: 2.5 hours
10. ABQ to Gallup 2 hours
11. Gallup to Flagstaff 3 hours
12. Flagstaff to Kingman 2 hours (includes Williams and Seligman)
13. Kingman to Barstow 3 hours (Includes Oatman and Cool Springs)
14. Barstow to Santa Monica 2 hours (Includes Victorville.)

If you can afford more than 2 weeks, then you can stay longer, a few nights in some of the stops.

Also, don’t forget that there are some pretty memorable side trips you might want to consider.

• Santa Fe New Mexico was once part of Route 66, then got wiped out with a new alignment. A visit to one of America’s most memorable and historic cities is one hour off the route, and of course one hour to get back.
• The Red Rocks of Sedona is just about a half-hour drive from Flagstaff. 
• The Grand Canyon, one of the great wonders of the world, is about an hour north of Williams.
• Once you hit Kingman, AZ, a detour to Las Vegas is roughly 90 minutes off the route.
• And when you get to Amboy, CA, a side road will welcome you to a two hour drive to Joshua Tree National Park.Remember to plan ahead, pick and choose, have fun, take your time, see the USA. if you have any questions about your Route 66 planning, travel photography or whatever, I’m one click away–photowalkstv@gmail.com I can’t wait to hear from you–and get back into the open road!