V-Twin Visionary’s Route 66 Centennial Ride

In 2026, the United States celebrates the 100th anniversary of U.S. Route 66, known worldwide as the "Mother Road." Established on November 11, 1926, the 2,448-mile highway from Chicago, IL to Santa Monica , CA. This very road serves as a living monument to American history, adventure, and the spirit of the open road. V-Twin Visionary is riding it in honor of Route 66’s 100th birthday! And we are inviting YOU to join us!

We of course are doing it “our way” and we are doing it backwards. Starting off July 13th at 12 noon in sunny Santa Monica California, we are kickstands up from our staging area at the Santa Monica pier and riding with friends old and new 2,448 miles through California, Arizona, New Mexico, Texas, Oklahoma, Kansas, Missouri, and Illinois ending up in Chicago.

If you are interested in joining the fun, contact us via DM or by emailing us directly from the contact page on vtwinvisionary.com. We will have a list of hotels to stay at along the way, daily morning meet-up points, designated lunch stops, as well as a list of motorcycle-friendly, fun, and interesting places to see along the way. Yes, doing this ride is going to be a great time, but as we all know the journey of miles is what this monumental ride is all about. So make plans to join us and be part of this bucket-list event!

For over a century, Route 66 has epitomized the aspirations and promises of the open road. A uniquely American icon whose enduring legacy has drawn millions westward from Chicago to the sun-kissed shores of Santa Monica at the ever-popular "End of the Trail" sign , which serves as an iconic, scenic western terminus. Although it was a U.S. highway for less than six decades, Route 66 continues to captivate and entertain enthusiasts worldwide. California encompasses 315 miles of the original route, with over 90 percent still navigable today, including hundreds of distinctive sites and attractions from its 20th-century zenith. 

Initially declared a federal highway in 1926, The popular connector was constructed on the remnants of the National Old Trails Road, a transcontinental path established by indigenous peoples and early European settlers. Historically, the official endpoint in Los Angeles was Lincoln and Olympic Boulevards. In 1935, it was formally extended to the city of Santa Monica, 13 miles west, where U.S. 66 merged with U.S. 101A. Symbolically acknowledging Route 66’s conclusion, the widely photographed “End of the Trail” sign at the Santa Monica Pier was erected in 2009 adjacent to Pacific Park and one of Santa Monica Travel & Tourism’s visitor center locations. 

Route 66 has evolved into a potent symbol of America, a nostalgic memory lane of weathered signs, vibrant neon lights, eccentric roadside attractions, and numerous mom-and-pop gas stations catering to weary drivers. Despite being decommissioned nearly four decades ago, Route 66 continues to endure through the dedicated efforts of enthusiasts, historians, preservationists, and merchants. While U.S. 66 is no longer featured on official road maps, Route 66 remains a vibrant and enduring symbol of American heritage.