We Rode 2,448 Miles for a Hot Dog

Friday 🗺️ August 7, 2026 🗺️ Route 66 Finale

Happy Friday, Reader!

We made it to Chicago! I think we are still buzzing from crossing the finish line. Or maybe that’s exhaustion from the 2,448-mile journey from Santa Monica we started back in February, lol. We cruised the last stretch from Springfield to Chicago this week and closed out Route 66 the same way we opened it, on the motorcycle. We even crossed paths with Big Boy heading south out of Chicago, which was an unexpected but happy surprise!

The Navy Pier was our big finish line for this wild Route 66 ride, and let me tell you, it totally lived up to the hype!

Lake Michigan caught us off guard before we even made it to Navy Pier. The air was thick with that humid summer smell, a mix of sun-baked stone, a hint of fish, and a whole lot of hot dog goodness wafting over from somewhere down the pier. We parked the bike and just stood there for a minute, soaking it all in. Route 66 started right here in Chicago, and here we were, back at the beginning.

Next up, we went on a wild goose chase for the 'End of the Route' sign. Instagram promised it was a mile or so off the pier, so we hopped in a pedi-taxi and zipped over to the supposed spot. Spoiler alert: there was nothing there. Just a random corner and a driver who gave us a shrug. So, we grabbed some bikes and pedaled our way back to the pier, sweaty and cracking up the whole way. Just another classic Route 66 misadventure for the books!

The pier itself was a whole adventure. There was music from a busker, kids shrieking on the Ferris wheel, and the smell of hot dogs and popcorn so strong you could practically taste it. I had to try a Chicago dog (obviously), and even though there was a sneaky Serrano pepper hiding inside, it was the perfect way to wrap up the day.

I was hoping to snag a shot of the skyline to celebrate rolling into Chicago, and somehow I lucked into this one. A gull swooped low over the water just as the skyline lit up with this dreamy, hazy light. Between that photo and the hot dog, I’d say the day was a total win!

The neon popped on just as the sky turned this perfect shade of pink behind it. If you’re cruising Route 66, you’ve got to stop at Legends Neon Park at dusk. Trust me.

The new guy on shift used to have to climb up into that rooftop phone booth during storms and call the siren down himself. Talk about motivation to move up the ranks fast!

The giant stood there holding his hot dog like a pro while a 1959 Cadillac waited at the curb, looking like it had never left the good old days.

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The Gemini Giant was born out of the space race, and he (I like to call him Gary) totally kicked off my obsession with these roadside giants. It was awesome to finally meet him in person!

Black smoke billowed from the stack and the ground actually shook as Big Boy rumbled his way from Chicago to St. Louis.

One Thing to Know: Travel Photography

That gull shot? Total accident. Travel photography is all about those happy surprises just as much as planning ahead. I always say, shoot wide and see what pops up. You never know what’s going to wander into your frame. The best photos are usually the ones you didn’t even see coming.

Next up: the Badlands of South Dakota, with a quirky Harvest Host stop on the way! And don’t worry, I’m already cooking up some Route 66 special issues to share more of the cool stuff we found. If there’s anything you’re curious about, just holler!

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