Chicago, IL
The symbolic beginning. The point where the idea became a real ride instead of just another travel dream.
I started this story on the eastern half of the Mother Road. Now the next chapter is forming: Amarillo to Santa Monica for the Route 66 Centennial, told through photography, road notes, coffee stops, and motorcycle miles.
Planning note: route details, timing, lodging, and participation options may evolve as the 2026 plan develops.
Last year’s Route 66 chapter carried the ride from the historic starting point in Chicago toward Amarillo — about 1,500 miles of motorcycles, photos, small towns, roadside oddities, coffee, weather, and the kind of memories that make a road feel personal.
The symbolic beginning. The point where the idea became a real ride instead of just another travel dream.
Historic towns, old-road energy, and the first rhythm of a long motorcycle story.
Small towns, classic roadside character, and the shift from Midwest memory into plains and western distance.
VW Slug Bug Ranch, Groom’s giant cross and leaning tower, and those unexpected places that make Route 66 feel strange in the best way.
The endpoint of the first chapter — and the launch point for the next one.
The next planned leg points west: New Mexico, Arizona, the Mojave, and finally Santa Monica.
Route 66 was commissioned in 1926. That makes 2026 more than another road-trip year — it is the centennial of the most mythic highway in America. For a rider, that changes the assignment. You are not just collecting miles. You are entering a story that has been shaping American movement for a century.
The Rocke approach is simple: show up with intention, ride with respect, and document the road while it is having one of its biggest cultural moments.
Heat matters on a motorcycle. So does light. A late-September strategy gives the ride a better chance to avoid the worst of the summer extremes while also opening the door to better photography, calmer mornings, and more enjoyable stops through the desert and high plains.
This is not about rushing from checkpoint to checkpoint. It is about designing a ride that leaves space for the road to become a memory.
The working concept begins in Amarillo and continues west toward Santa Monica — a route that moves through the visual heart of the Mother Road: Texas Panhandle icons, New Mexico neon, Arizona desert towns, and the final pull toward the Pacific.
The goal is not simply to arrive. The goal is to build a ride with enough rhythm to stop, photograph, talk, drink coffee, and let the route tell its own story.
Every major motorcycle trip has two stories: the romantic story and the practical story. The romantic story is the open road. The practical story is lodging, heat, fuel, fatigue, return plans, and how to get the bike home.
RockeRide carries the operational details. RockePhoto carries the visual story. Together, the goal is to create a ride that feels meaningful without becoming chaotic.
The best rides are not only about machines. They are about people, timing, trust, and shared stories. This ride should feel small enough to be personal and structured enough to be memorable.
Photography is not a bonus here. It is part of the mission. The road deserves more than quick phone shots at gas stations. It deserves portraits, field notes, night neon, quiet coffee stops, and the imperfect moments that make a ride real.
The shop is not open yet, but this is where Route 66 digital items will live: ride guides, photo packs, printable road notes, maps, wallpapers, and collector-style downloads from the journey.
The digital shop is not open yet. For now, both support buttons open the current Buy Me a Coffee support hub: use “Buy Me a Coffee” for general support, or write “Sponsor a Mile” in the note when supporting the Route 66 ride.
↑ Back to topFor route details, ride logistics, and motorcycle-first updates, continue to RockeRide. For the visual story, stay here at RockePhoto.
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