Route 66 2027 — From Chicago to the Pacific

Welcome in Chicago, transfer to the hotel and technical briefing with the UpSerra team. Bike handover at the partner rental (BMW R1300GS), luggage rack fitting and test ride. Welcome dinner, classic American style — diner, burger, cold beer.

First contact with the Mother Road. Departure from the Begin of Route 66 sign in Chicago, crossing rural Illinois and the small historic towns that lived off the road — Springfield among them, where Lincoln built his political career before the White House. Across the Mississippi into St. Louis, Missouri, with the Gateway Arch framing the end of the day.

Classic Route 66 stretch, with neon diners, 1950s gas stations and towns that stood still when the interstates took the traffic away. We cross Missouri and the short — and mandatory — slice of Kansas. Overnight in Tulsa, Oklahoma.

The infinite horizons of Texas start here. Mandatory stop at the Cadillac Ranch — ten Cadillacs buried nose-down in the desert, covered in graffiti. Bring a spray can and leave your mark. Arrival in Amarillo, capital of the Texas Panhandle.

The longest riding day of the tour, and the one that changes the landscape completely. Into New Mexico and the colours of the American Southwest, following Route 66 across the high desert to Gallup — a town that grew on the road, surrounded by Navajo and Zuni territory.

The day of the West’s iconic landscapes. Past Shiprock, the volcanic formation sacred to the Navajo, and through Monument Valley — the red buttes that became the postcard of John Ford’s westerns. Overnight in Page, on the shore of Lake Powell and minutes from Horseshoe Bend.

A short day on the handlebars and a long one on scenery. Crossing Grand Canyon National Park along the South Rim viewpoints, with colours shifting from red to purple depending on the hour. Overnight in Williams, the village that reinvented itself as the capital of Route 66 tourism, with themed bars and the historic railway station.

Probably the most cinematic day of the tour. Route 66 nostalgia in Seligman (the village that inspired Pixar’s Cars), a stop at the Hackberry General Store, and the technical challenge of the Sitgreaves Pass dropping into Oatman — a mining town with wild burros walking freely down the main street. Crossing the Hoover Dam and arrival under the lights of the Las Vegas Strip.

First day off the bike after eight on the road. Cirque du Soleil show, premium dinner, the iconic Strip casinos, pool party — or simply sleeping in. Each rider lives their own Vegas.

A rest day in the city that never sleeps. Cirque du Soleil show, premium dinner, the iconic Strip casinos (Bellagio, Caesars, MGM), pool party, or a day trip to Red Rock Canyon or Valley of Fire. Each rider lives their own Vegas.

Crossing the Mojave Desert (alternate route to Death Valley to avoid extreme October temperatures). Approach to Sequoia National Park, riding the Kern River Canyon with its red gorges. Overnight in Kernville, a mountain village with an outdoorsy vibe.

We cross Sequoia National Park end to end on the park’s most cinematic roads: Kern River Road, California Highway 99, Tunnel Rock, Tunnel Log, and a stop at the General Sherman Tree — the largest living tree on the planet by volume (84 m tall, 31 m around). Descent to Fresno.

The day to close the loop. Descent through inland California to the Santa Monica Pier, the mandatory photo under the “End of the Trail” sign — the point where Route 66 ends, on the Pacific. Closing toast with the team.