Route 66 2027 — From Chicago to the Pacific

Welcome in Chicago, hotel transfer, technical briefing with the UpSerra team. Bike pickup at the partner rental shop (Harley-Davidson Touring or BMW R1300GS per booking), luggage rack adjustment and test. Classic American welcome dinner — diner, burger, cold beer.

Departure from “Begin of Route 66” in Chicago and immediate dive into deep America — 1950s diners, small towns that lived and died with the road. Crossing the Mississippi to St. Louis, the iconic Gateway Arch framing the sunset. Overnight in the city that was the gateway to the 19th-century American West.

Classic Route 66 stretch with stops at neon diners, historic 1950s gas stations and traditional towns that lived off the road’s traffic before the interstate era. Crossing Missouri and Kansas. Overnight in Tulsa, Oklahoma — cowboy country.

The infinite Texas horizons begin here. Mandatory stop at the Cadillac Ranch — an art installation of 10 Cadillacs buried vertically in the desert, covered in graffiti (you can bring a spray can and leave your mark). Arrival in Amarillo, capital of the Texas panhandle.

Up to the New Mexico plateau. Santa Fe is one of the oldest cities in the US — preserved Spanish colonial architecture in adobe, indigenous art galleries and authentic Tex-Mex cuisine. UNESCO-listed historic center. Overnight in Santa Fe.

The day of iconic western landscapes. Passing Shiprock (a sacred Navajo rock formation) and arrival at Monument Valley — the red buttes that became postcards of John Ford westerns and Forrest Gump. Overnight in Kayenta, inside the Navajo Nation.

Crossing Grand Canyon National Park — one of the most imposing landscapes on the planet. South Rim viewpoints, colors that shift from red to purple depending on the hour. Overnight in Williams, a village that reinvented itself as the Route 66 tourism capital with themed bars and a historic train station.

Probably the most cinematic day of the tour. Nostalgia dive in Seligman (the village that inspired Pixar’s Cars), stop at Hackberry General Store, technical Sitgreaves Pass descent to Oatman — a mining village with wild donkeys roaming the main street. Crossing the Hoover Dam and arrival under the lights of the Las Vegas Strip.

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

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

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

Closing the loop. Descent through interior California to the Santa Monica Pier — mandatory photo under the “End of the Trail” sign where Route 66 ends, at the Pacific. Closing toast with the UpSerra team.

Day to explore Los Angeles: Hollywood, Beverly Hills, Venice Beach, Walk of Fame, Griffith Observatory. Or just stay at the Pacific watching the sunset on the beach. You crossed a continent on a motorcycle — you earned it.

Bike return at the partner rental shop in LA. Transfer to LAX airport and flight home. For those who want to extend, UpSerra advises options: Las Vegas one more day, San Francisco to the north, or Cancun on the way home.