It’s a wrap… for now

The Ultimate Route 66 Adventure: From Chicago to Santa Monica

Thirty Eight days and countless adventures later, Janet and I finally picked up the keys for our road trip—two weeks of laughter, mischief, and discovery along the historic Route 66. Starting in Chicago, Illinois—the birthplace of this legendary highway—we couldn’t wait to dive into the ultimate American road trip. The first stop: the Museum of Ice Cream, followed by a visit to Chicago’s famed Second City. As we posed for pictures and explored, we met some friendly faces and even used a “get out of jail free card” in true road-trip fashion!

Everything about Route 66 is big, bold, and fun. From the towering St. Louis Arch to the eccentric, larger-than-life roadside attractions, there was never a dull moment. We even ran into a pink elephant and a blue hippo along the way—random? Yes. Fun? Absolutely. We couldn’t resist making a stop at the Uranus Fudge Factory, grabbing a couple of sweet treats. After all, what’s the point of fudge, if not to enjoy it at a place that’s a little… out there?

The road led us to the crossroads of three states at the "Point of Confusion," and we couldn’t help but snap a picture with the cars from the Cars movie at a quirky pitstop. But it wasn’t all about the fun and games—sometimes, the bathrooms were hilarious enough to make a whole pitstop worth it. And then there were the iconic stops like the Slug Bug Ranch and the Rebel Combine—each one a bizarre delight.

Driving on, we encountered the Musical Highway, Tinkertown Museum, and even PistachioLand—though the three-hour detour to get there felt like a very long detour thanks to a slow-moving flatbed truck. But hey, it was all part of the adventure. Eventually, we made it to Horseshoe Bend and the Grand Canyon, where we marveled at the Painted Desert and the Petrified Forest, even driving through a tree along the way.

One of the most unforgettable stops was Four Corners, where we stood in awe at the unique place where Arizona, New Mexico, Utah, and Colorado meet. We were all set to see Grand Falls, but it had dried up, leaving us with a sense of bittersweet nostalgia. But no worries—we were back on the road, crossing into Winslow, Arizona, where we stood on the famous corner. (Yes, we sang the Eagles song, just like everyone else.)

Sedona’s turquoise arches at the McDonald's were picture-perfect, and we drove the 191 curves on the wild road to Oatman, Arizona—a thrilling 8-mile stretch that definitely earned its reputation. Elmer’s Bottle Tree Ranch and Red Oaks II were more quirky spots that made the road trip truly one-of-a-kind.

We drove through the Rim of the World, got a peek at the first McDonald's in San Bernardino, and took a moment to dip our toes in the Pacific at the end of Route 66 in Santa Monica. The end of the road didn’t feel like an ending at all—it felt like another beginning. Along the way, we sipped wine, drove the 17 miles of Pebble Beach Drive, and almost stayed in a hotel with ghosts.

Somewhere along the way, we stopped for the Jelly Belly Tour, drove over the Golden Gate Bridge (which, by the way, is made to swing), and marveled at the Miracle Staircase in Santa Fe, New Mexico. Crater Lake National Park was next on our list—amazing views and snow at 82°. The natural bridges were also incredible, but nothing topped Yellowstone National Park’s geysers and Devil’s Tower, which made for a perfect end to the natural wonders section of our trip.

Of course, no trip through the heart of America would be complete without stops like the Corn Palace in Mitchell, South Dakota, and Sioux Falls’ stunning pink quartzite waterfall. A detour led us to Bluebonnet Ice Cream, and we made it a point to see family, although Peggy convinced the waiter that Janet was losing her mind (Loco Poco, anyone?). From Tom Sawyer’s ice cream to a wild storytelling stop in Missouri, our days were packed with surprises.

What made this entire trip truly unforgettable wasn’t just the landmarks or the wild detours—it was sharing it all with Janet. She’s the kind of person you want with you on an adventure like this, someone who keeps the spirit alive with laughter and a sense of spontaneity. From start to finish, this was a road trip for the books—and I wouldn’t want to take it with anyone else. Actually Janet did most of the driving. She said Ditto about the trip. Two kernels in a corn cob.