Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Well folks, we did it again. Another one of our legendary road trips, the kind that require a decent amount of snacks, an epic roadtrip playlist courtesy of Ivy and her Dad, and the occasional “where is the next bathroom?” moment. This time, the backdrop was none other than Route 66 on the way to Zander's final Varsity Arizona baseball tournament. And by "final," I mean the kid is a senior and this is the last time we’re off on a big trip to watch him play.. But hey, we weren’t just heading to Arizona for the tournament. Nope, we’re a road trip family. Partly because we love it, and partly because it’s way cheaper than flying (have you seen ticket prices these days?). Plus, there’s the added bonus of endless hours in the car to bond… or get on each other's nerves. It’s basically a rite of passage.

So, instead of enduring the packed airports and cramped airplane seats, we loaded up the car, packed a few too many snacks (I mean, what’s a road trip without a full inventory of chips, candy, and the occasional fruit for health's sake?), and set off to make the most of the drive to Arizona.

Our first stop? Winslow, Arizona. Cue the music. “I’m standing on a corner in Winslow, Arizona...” Yeah, I know you sang it in your head, and I’m not apologizing for it. It had to be done. But seriously, it’s a tiny little town with a giant statue commemorating the Eagles’ famous song, “Take It Easy.” As much as I’d like to pretend we took the time to explore the deep cultural history of Winslow, the truth is, we were mainly there to take a cheesy family photo with the statue. Don't judge us. If you ever find yourself there, it’s like a mini pilgrimage for anyone who grew up listening to classic rock. And we did. Like, a lot.

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

After a quick "we're here, let's take a picture and eat some ice cream" moment, we continued our journey down the Route 66 highway. But wait, there’s more! (Isn’t there always?) Next up, Twin Arrows Trading Post. Well, singular Twin Arrow now, thanks to some seriously wild winds. The second arrow? Yeah, it's more of a suggestion at this point. Still, we had to stop and gawk at what was left of the old place. I know, I know—it’s one of those roadside attractions you see online and wonder if it's worth it. But hey, when you're on Route 66, you stop at these weird landmarks because, well, when else will you get to see a giant arrow that’s been partially blown away? Exactly.

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

We took a few photos (because, hello? Photographer here!) and headed off to the tournament. That was not fun, so I wont go into detail. Poor Z caught a nasty cold and his team…well, let’s just say they’re not winning many games these days.

Zander’s team wasn’t scheduled to play until 7PM so we got permission to take him to the Grand Canyon. Because what would a road trip be without seeing something so jaw-droppingly beautiful that it almost makes you forget how many hours you’ve spent in the car? For those who haven’t been, let me tell you: it’s the real deal. I could have wandered around photographing it for days. You stand there, gazing into the abyss, and all of a sudden, you feel very, very small. Like, “Wow, I could fall into this thing and nobody would even notice” small. It’s humbling. And a little terrifying. But mostly awe-inspiring.

Zander said it was one of the highlights of the trip (way better than being sick and watching his team blow it again) and we took tons of photos (a few of which scared me more than just a little) just so we could have some evidence that we made it to one of the Seven Natural Wonders of the World.

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

After yet another loss, we grabbed Z and made tracks to Sloane Park to watch our beloved Cubbies! You know, a real baseball team who can really play? No big cameras allowed, but be assured we had more fun than was reasonable and we wont discuss just how much we spent at the team store on merchandise. Seriously…leave that one alone.

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Off to Flagstaff, AZ and the Galaxy Café. Yes, this was strategically planned to coincide with the need for milkshakes. I’m talking thick, glorious milkshakes that can be considered a meal, not just a beverage. You know the ones that come with a hefty amount of whipped cream and a sprinkles on top, and they make you wonder, “Can I have this for breakfast tomorrow?” The answer was, of course, was a no because we left super early the next morning…but a girl can dream.

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

And just when we thought the trip couldn’t get any better, we arrived at the Wigwam Motel in Holbrook, Arizona. Now, before you start imagining some old-fashioned charm with, you know, cozy little wigwams with dreamcatchers and maybe a peaceful nature soundtrack playing, let me clarify: this place is a quirky, vintage, throwback to a time when road trips were an American pastime and the gas stations sold maps with promises of amazing roadside attractions. The wigwams are concrete, not exactly “cozy” per se, but they’re certainly something you won’t forget. I mean, where else can you sleep in a giant concrete teepee? Ivy totally wants to go back and stay.

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Next up: the dinosaurs. Ah yes, Holbrook also boasts some seriously weird roadside dinosaurs. We're talking giant, 25-foot-tall fiberglass beasts, casually hanging out on the side of the road. We didn’t just drive past; we stopped, got out, and spent way too much time posing by these over-the-top sculptures. I like to think that the dinosaurs enjoyed the attention, but honestly, it felt like we were the ones who were getting judged. It's a good thing nobody else was around, or we would’ve never been allowed back into polite society.

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

One final stop!  No way were we going to pass up the Jackrabbit Trading Post!  It was closed (because...Sunday) but the Cars movie lovers that we are, we NEEDED a picture with that epic sign.  Ivy and her dad were more than happy to jump on the big jackrabbit for a quick, "We're such tourists!" photo.

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

Route 66 Road Trip: Baseball, Dinosaurs, and Milkshakes (Because Why Not?)

So, take it from me: if you’re looking for a budget-friendly, slightly absurd adventure, get yourself on Route 66 and embrace the weirdness. Who knows, you might just find yourself standing on a corner in Winslow, Arizona, singing with the Eagles, and realizing that the road trip, not the destination, is half the fun. Enjoy the photos, and maybe we’ll inspire you to take your own crazy road trip. Just don’t forget the milkshakes. Or the dinosaurs. Or the wigwams. Seriously. Don’t miss out.

Until next time, folks—safe travels, weird stops, and a lot of snacks.

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