Route 66 — the Mother Road. The highway that stitched America together, carried dustbowl migrants westward, birthed motels with neon buzz and chrome diners with bottomless coffee. In 2026, Route 66 turns 100, and EagleRider—the global name in motorcycle adventures—is marking the century in style.
This isn’t your run-of-the-mill group ride. EagleRider has announced the Route 66 Centennial Tour, a 16-day, Chicago-to-Santa Monica odyssey that will see just 66 riders worldwide experience history in motion. Departure day is locked in for June 23, 2026, and the numbers couldn’t line up more perfectly: 66 riders, on Route 66, celebrating 100 years of the road as America itself marks its 250th birthday. You can’t script it better.
“This ride defines what it means to be a true rider: two great American milestones, one legendary road and endless adventure,” says EagleRider CEO Sebastian Schoepe. “When the numbers align like this, you don’t question it—you twist the throttle.”
The Ride of Rides
Over 2,200 miles and across 8 states, the Centennial Tour promises to hit every iconic landmark along the route. Think Cadillac Ranch in Amarillo, where upended cars stand as steel sculptures in the desert. The Blue Swallow Motel, a neon beacon from Route 66’s golden age. Oatman, Arizona, a half-forgotten Wild West town where burros still wander the streets. And, finally, that victorious roll onto the planks of the Santa Monica Pier—the symbolic end of America’s most storied highway.
It’s more than a guided tour. It’s a celebration of the very spirit of riding: freedom, history, and camaraderie.
Tulsa Takeover
Midway through, the group descends on Tulsa, Oklahoma just as the city throws its biggest Route 66 bash: the AAA Route 66 Road Fest (June 27–29, 2026). Expect classic cars gleaming under the sun, live music echoing through the Expo Square’s SageNet Center, and enough memorabilia to make any collector grin. Riders can dive into the festival or simply use the stopover to soak up Tulsa at their own pace.
Once-in-a-Lifetime Kit
Every rider lucky enough to snag a spot receives a Centennial Tour Riding Jacket, designed exclusively for this event. It won’t be sold. It won’t be reproduced. Just 66 jackets for 66 riders. A collector’s piece you’ll wear with pride long after the tyres have cooled.
The EagleRider Touch
Of course, EagleRider isn’t just about pointing you down the road and waving goodbye. The package includes:
* Premium hotels at every stop
* Professional, multilingual guides
* Support vehicle assistance (so you can ride light)
* Daily breakfast and fuel on riding days
* Luggage transport
* A farewell party at the finish line
And the machines? Riders can choose from Harley-Davidson Touring models, BMW’s R1250, or Yamaha’s Ténéré 700 for the more adventure-minded. Pricing starts at $7,047 per rider (based on dual occupancy).
A Ride That Writes Itself
There are plenty of epic journeys in the world — Alpine passes, desert tracks, Pacific coastlines — but nothing else carries the same weight as Route 66. It’s not just about the scenery. It’s the open road, nostalgia and freedom, and the chance to be part of a centennial story.
Spots are limited, and once those 66 are taken, that’s it. No reruns, no waiting list for next year. Route 66 only turns 100 once.
For more details or to see if one of those golden spots could be yours, visit EagleRider’s Centennial Tour
Route 66 Centennial Tour at a Glance
Day 1 – Chicago, IL
Arrival, orientation, and welcome dinner in the Windy City.
Day 2 – Chicago to Springfield, IL (203 mi)
Pick up bikes, visit the Pontiac Route 66 Museum, and roll through Illinois farmlands.
Day 3 – Springfield to St. Louis, MO (92 mi)
Cross the Mississippi on the Chain of Rocks Bridge into the Gateway City.
Day 4 – St. Louis to Springfield, MO (216 mi)
Ride the Missouri Ozarks, classic diners, and small-town Americana.
Day 5 – Springfield, MO to Tulsa, OK (181 mi)
See the Rainbow Bridge in Kansas, then cruise into Tulsa’s Art Deco charm.
Day 6 – Tulsa, OK
Free day with optional Centennial Road Fest celebrations.
Day 7 – Tulsa to Oklahoma City (106 mi)
Highlights include Arcadia’s Round Barn and the neon soda bottle at POPS.
Day 8 – Oklahoma City to Amarillo, TX (260 mi)
Chisholm Trail history, Route 66 Museum, and the Big Texan Steakhouse.
Day 9 – Amarillo to Santa Fe, NM (279 mi)
Cadillac Ranch, ghost town of Glenrio, and into the high plains of New Mexico.
Day 10 – Santa Fe, NM
Rest day with optional Taos ride, hot air ballooning, or exploring historic Santa Fe.
Day 11 – Santa Fe to Gallup, NM (198 mi)
Through Albuquerque, Laguna, and Navajo country into Gallup.
Day 12 – Gallup to Flagstaff, AZ (185 mi)
Ride the Petrified Forest and classic Route 66 towns like Winslow.
Day 13 – Flagstaff to Kingman, AZ (146 mi)
Seligman’s retro revival and desert highways into Kingman.
Day 14 – Kingman to Victorville, CA (206 mi)
Twist through Oatman’s burro country and across the Mojave Desert.
Day 15 – Victorville to Los Angeles, CA (138 mi)
Angeles Crest Highway, then the final roll onto Santa Monica Pier.
Day 16 – Los Angeles, CA
Farewell breakfast and departures.
