Motorcycle Trip Route 66 from Seattle area to Los Angeles to Chicago then back to Seattle via the Trans Canadian Highway. June 12, 2025 Thru July 2, 2025.


A map of the route from home to Los Angeles then along Route 66 to Chicago. I then went north to Canada (I love visiting Canada) and took the Trans Canadian Highway back home. This trip was a slow ride across the United States to see the America that everybody bypasses when they drive the interstate. THEN I got the see the amazing counbtryside of Canada riding along the Trans Canadian Highway, a better ride than I expected to be honest. A total of 6,315 miles.

Going from Los Angeles to Chicago in the air conditioned car flying past towns while on the Interstate is not really 'seeing' the country or experiencing the moment and environment you are in for me. If you want to travel Route 66 the fast way, take Interstate 15 to I-40, over to I-44 then I-55 into Chicago, and 30 hours later you have (essentially) travelled Route 66. I wanted a more tactile experience, making 'good time' with emphasis, as Robert Pirsig says, on 'good' rather than on 'time'. Traversing the countryside and going THROUGH the towns, not around them, that previous travellers had gone through 100 years ago was the experience I was looking for. I knew that it could never be the same perspective, towns had grown and shrank. Stoplights were installed. But just encountering the country at a slower pace was what I was interested in.

Riding on a motorcycle gives yet a different experience then traversing Route 66 in a car. From 'Zen and the Art of Motorcycle Maintenance' by Robert Pirsig comes the following quote:

You see things vacationing on a motorcycle in a way that is completely different from any other. In a car you're always in a compartment, and because you're used to it you don't realize that through that car window everything you see is just more TV. You're a passive observer and it is all moving by you boringly in a frame.

On a cycle the frame is gone. You're completely in contact with it all. You're in the scene, not just watching it anymore, and the sense of presence is overwhelming. That concrete whizzing by five inches below your foot is the real thing, the same stuff you walk on, it's right there, so blurred you can't focus on it, yet you can put your foot down and touch it anytime, and the whole thing, the whole experience, is never removed from immediate consciousness.

I have created a page with JUST the planning for the trip including all the very specific waypoints for navigation if you want to make the trip yourself:
Route 66 preparations and GPX waypoints

I have created a page with JUST the planning for the trip including all the very specific waypoints for navigation if you want to make the trip yourself:
Route 66 preparations and GPX waypoints

Adam, Meandering Miles (on BlueSky) interviewed me about the Route 66 and the Trans Canadian Highway ride and put it on his Meandering Miles YouTube page where he has interviews with other riders and documents his OWN adventures.

The Twenty One day trip

Seattle To Los Angeles (The Start) - 3 Days

Los Angeles to Chicago (Route 66 Ride) - 10 Days

A map of the entire ride from Los Angeles to Chicago, descriptions of riding the route are in the details below:



Chicago to Canada then Home (Trans Canadian Highway Ride) - 8 Days

Riding back home after Route 66, riding the Trans Canadian Highway, the entire map for this portion of the ride, details for each day are in the links below:

Motorcycle Trips



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