Popular with commuters and located near the start of the mother road, apparently this place is the place to stop before you start out. They’ve been feeding hungry travelers since 1923 and if the food is in real life anything like the pictures, I can see why. (The whole How It’s Made page makes me want to put the kids in the car and drive to Chicago for breakfast.)
Cuba is a pretty cool place; they have the murals. This is a modern roadside attracting in the great tradition of them, and the pictures featured in the Atlas Obscura article capture the fun of roadside attractions. Apparently it actually had to be welded in place once it made the Guiness Book because when it rocked, it was terrifying. You can only sit on it one day a year, but those pictures prove you don’t need to sit on it to enjoy it.
It’s a barn that looks like a fat, short silo and it’s awesome. It was built in the 1890s, made it onto the National Register in the 1970s, and was rebuilt in the 1990s by a group of volunteers (and let me take a moment to say: bless the volunteers, for without them, what would we have left of our cultural resources?). And it’s a museum!
This is a bunch of Cadillac bodies half-buried in the dirt on a farm. This place was an enduring myth of my childhood, and little under five years ago, I finally got to see it. My sleeping kid tossed over my shoulder, I made the walk beside my mom, who wasn’t quite a teenager when it was first installed. It was a really neat experience.
The oldest church in the US and on the National Register and absolutely one of the prettiest places to stop. They even still hold Mass, and I’m not Catholic but there’s always something really profound about religious services held in old places. For a dose of even more history, and a bonus entry-within-an-entry, you can also check out the oldest house in the US, the De Vargas Street house, which was built in the remains of an ancient pueblo.
I could have gone with the Grand Canyon, and you totally shouldn’t miss it if you’re doing this road trip, but I love the Petrified Forest National Park. I love the badlands, I love that this is the only national park to actually preserve a piece of the original Route 66, and I love all the trees that look like rocks (there’s even a thing called the Little Lithodendron Wash, and “lithodendron” literally means “rock tree”). It’s a nice stop on the way to Flagstaff, which is easily my favorite city on the whole road trip.
The most recently-nominated “end point” of Route 66, the pier is over 100 years old and the website has the niftiest timeline feature. There’s plenty of fun to be had and food to try, and Santa Monica is a pretty cool city in general. Not a bad way to end a trip.