ON THE ROAD AGAIN: 2LANELIFE’S ROUTE 66 RUN

In 2020, we set off on one of our longest motorcycle journeys at the time and rode the Historic Route 66 end-to-end from Santa Monica, California to Chicago, Illinois with some incredible adventures along the way. We experienced so much history, great food, inspiring stories, and cool landmarks, and it made for an unforgettable adventure.

Although it was nearly six years ago, we often reminisce on this trip as one of our favorites and we find ourselves recommending it to first timers when visiting the states or looking for a first big ride to explore some of America’s history. Whether it be the entire route or just a portion at a time, Route 66 has something for everyone.

Now the kicker…WE’RE DOING IT AGAIN in 2026 for the 100th anniversary of Route 66! That’s right, we’re riding the Mother Road end-to-end again, this time starting in Chicago and riding to sunny Southern California to finish at the Santa Monica Pier. This time around, we are going to dive deeper into a lot of the history and do our best to visit some historic sites and small towns that we skipped on our initial journey. To truly see and experience everything that The Mother Road has to offer, it would take months if not longer, but we’re going to do what we can and involve ourselves in the communities along the way as much as possible.

Few highways carry the cultural gravity of Route 66. Commissioned in 1926, the “Mother Road” became a lifeline during the Dust Bowl, immortalized in The Grapes of Wrath, and later symbolized postwar freedom as families headed west in search of opportunity, sunshine, and reinvention. Stretching from Chicago to Santa Monica, Route 66 stitched together small towns, neon-lit motels, trading posts, diners, and desert outposts into one continuous American story.