Riders on Royal Enfield’s relay team just wrapped a 2,400-mile run down Route 66, tracing the full length of the highway from Chicago to Santa Monica to mark 125 years since the brand was founded in Redditch, England, back in 1901. The ride split into four legs of roughly 500 to 600 miles apiece, carrying the celebration across eight states.

Chicago to Santa Monica, One Leg at a Time

According to Royal Enfield’s own announcement of the ride, the relay departed Chicago on August 27, 2026, and reached Santa Monica by September 7, covering the entire historic Route 66 corridor. Each of the four legs was handed off to a different rider, all of them content creators tasked with documenting their stretch of highway for the brand’s North American social channels, with the company noting each rider brought “their own perspective and personality to the road.”

Key Points

• Distance: 2,400 miles from Chicago, Illinois to Santa Monica, California
• Format: Four relay legs of about 500-600 miles each, across eight states
• Dates: Departed August 27, 2026, arrived September 7, 2026
• Motorcycle used: Royal Enfield Classic 650 125th Anniversary Edition
• Milestone marked: 125 years since Royal Enfield’s founding in Redditch, England, in 1901

The route wasn’t a random pick. Royal Enfield’s own materials describe Route 66 as a road that “has become synonymous with the American spirit of motorcycling freedom and adventure for the last century,” and the timing lines up with Route 66 itself marking its own centennial in 2026, giving the brand’s anniversary ride a second milestone to lean on along the way.

A Bike Built for the Occasion

The relay ran on Royal Enfield’s Classic 650 125th Anniversary Edition, a limited model built specifically around the milestone. Motorcycle.com’s coverage of the anniversary lineup describes the edition as finished in classic red with gold-embossed 125-year crests and a distinctive “hypershift” paint treatment, released in Europe starting in August. Royal Enfield paired that bike’s launch with a broader push tying together its history and its current lineup, including a display spanning five generations of machines, from a replica of the original 1901 model to a restored 1932 Bullet.

Part of a Bigger Anniversary Year

The Route 66 relay is one piece of a longer 2026 calendar for Royal Enfield’s 125th. Cycle News reports that the brand has run an expanded program of events across the U.S. and Canada throughout the year, including Classic 650 test rides at Daytona Bike Week, dealer open houses, and its Build.Train.Race road and flat-track series at venues including Road Atlanta, Road America, and Ventura Raceway. Taken together, the cross-country relay functions as a rolling capstone to a company that has spent the better part of the year putting its anniversary in front of riders in person, one event and one highway mile at a time.