We started where everyone ends

Happy Friday, Reader!

We finally landed at an RV park after more than a hundred days on the road, and let me tell you, a long shower and endless air conditioning feel like winning the travel lottery. While I’m soaking up these little luxuries (and catching up on editing, of course), I took a stroll down memory lane and picked out five Route 66 moments that totally caught me off guard. The first surprise? It happened before we even rolled out of the parking lot.

Silhouette of the Santa Monica Pier at sunset, with the Pacific Park ferris wheel and roller coaster against a deep orange sky and small figures walking on the beach below. — Santa Monica Pier at sunset

The sun was sinking behind the Ferris wheel, and there I was, camera in hand, snapping that classic Route 66 shot: sun, silhouettes, the whole works. Most folks finish their journey here, soaking in the sunset after 2,448 miles of adventure. But not us! We were just getting started at mile zero, truck and trailer pointed east, ready for whatever weird and wonderful things the road had in store.

Here's where I got my first Route 66 surprise: the pier isn't actually the end of the road! The real finish line is a few blocks away at Santa Monica Boulevard and Ocean Avenue. There's just a tiny sign, no Ferris wheel, no crowd, no sunset magic. Most people miss it because they're busy taking the same photo I just snapped at the pier.

We actually stopped there for a late lunch before heading to the pier, and I snapped a photo of the sign without even realizing what it was. Not exactly a wall-worthy shot, but it’s a great reminder to keep an eye out for the unexpected. The next morning, we headed east, ready for more surprises.

That little fun fact set the vibe for the whole trip. Turns out, the most photographed spot isn't always the coolest, and sometimes the real gem is just a couple of blocks away from the crowd.

Iconic gas pump

I told myself I’d just snap one for the archive, but three towns later, my camera roll was overflowing with them. Oops!

The Blue Swallow Motel at night, with red neon outlining the roofline and a blue neon "Blue Swallow Court" sign glowing above purple garage doors. — Rooms with character at the Blue Swallow

We rolled in thinking we’d just grab the classic front-drive photo, but instead we ended up chatting with a guy about his antique car while a bunch of Italian tourists posed for their Instagram moments.

A weathered "Motel" and "Cafe" sign on a tall metal frame in the Glenrio ghost town, with a graffitied building on the left reading "Just Be" and a black truck towing a white RV parked on the right. — Glenrio ghost town

You can hear I-40 humming nearby from the cracked pavement, which somehow makes the silence in town feel like it’s there on purpose.

The three-story brick Beckham County Courthouse in Sayre, Oklahoma, topped with a copper dome and flying American and Oklahoma flags, beneath a dramatic cloudy sky over empty streets. — Beckham County Courthouse - Sayre, OK

I later learned that the Joad family rolls past this courthouse in the film The Grapes of Wrath, and the building hasn’t changed enough to notice.

Two small white and brown dogs standing in a gravel lot in the ghost town of Texola, Oklahoma, with a weathered green Route 66 "Tumbleweed" truck parked beside an abandoned yellow building. — Texola welcoming committee

We rolled into a town that looked totally empty, but two dogs came trotting out to greet us like we were the guests of honor they’d been waiting for all day.

One thing to know.

Route 66 has taught me a thing or two about chasing the perfect photo. The famous spot is hardly ever the only spot, and it's almost never the best one. If you hang around for just ten more minutes or wander off in a direction nobody else is going, you'll find the magic shots everyone else misses.

We've made it to Oklahoma, and I'm curious what surprises await in the second half. If you want to wander back through the first half of the trip, you can find it all right here.

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