Ken Hollis’ Route 66 and Trans-Canada Highway Road Trip
Connect with Ken Hollis
In this Miles Shared episode, I reconnect with Ken Hollis, a rider from the Seattle area who recently completed a ride many of us dream about. He followed historic Route 66 from Los Angeles to Chicago, then turned north and took the scenic route home—riding the Trans-Canada Highway all the way back to the Pacific Northwest.
Ken first appeared on Miles Shared a few months ago, when we was starting to plan his Route 66 adventure. Now, after riding over 6,300 miles across the U.S. and Canada, he returns with fresh stories, lessons, and a calm sense of presence that only a long road can bring. We talk about gear, serendipity, and a favorite quote from Zen and the Art of Motorcycle Maintenance that shaped his outlook on the ride.
What We Talked About
Why 2025 was the year for him do Route 66
The towns, roads, and detours that stood out—good and bad
The donkeys of Oatman, the diners of the Midwest, and the empty miles of the Trans-Canada
How it felt to be "in the scene" and not just observing it, as Pirsig described
Planning, weather, and the challenges of a three-week solo ride
What the road taught him—and what comes next
Gear, Resources, and Recommendations
EZ66 Guide for Travelers by Jerry McClanahan
Royal Tyrrell Museum of Palentology in Alberta, Canada
Georgia O’Keeffe Museum in Santa Fe, New Mexico
Gear, Resources, and Recommendations
Ken’s story is proof that you don’t need to rush. You just need a bike, a plan, and a willingness to go. This was a thoughtful, unhurried conversation about a truly meaningful ride. Check out his trip journal, or drop a comment on the video to let us know your favorite stretch of Route 66.
Thanks for riding along.