Dear Mom, Dad, Sis & Cat – My Motorcycle Trip – 1964/65

Story by Glenn Roberts//
August 29 2023

I suppose it happens to everyone at some point, to varying degrees: That stage in life when you just need to get away from the regular day-to-day of growing up, and into the stage of adulthood that comes with itchy feet and the need to explore. Jamie Smallwood grew up on the island of Montreal racing homemade go-carts down hills, defying gravity by jumping his bicycle over ditches and getting hurt — and, eventually, hot rods and girls came into the picture: You know, regular boy stuff.

His family life was good, and he had a steady girlfriend, but after graduating in 1964 he had an uncontrollable desire for adventure and the thought of a motorcycle trip entered his mind. His understanding father helped him purchase a motorcycle and by the fall of ’64 he had left his comfortable life and his girlfriend to “find himself.”

Dear Mom, Dad, Sis and Cat is the story of a 19-year-old Smallwood, who left home for a five-month motorcycle trip south of the border. The book is written by Smallwood himself, from memory, but also from letters he sent home and his diary that were “rediscovered” when he and his sister were downsizing his father’s processions.

The trip was spent circumnavigating the United States while trying to understand the political and racial tensions of the mid-’60s that were so foreign to him in Canada, and he explains the hardships of the road and looking for work in order to finance his travels, as well as the sadness of his first-ever Christmas away from his family and the love of his life.

Smallwood goes into detail of his time spent in Florida working at an orange grove, handing out soap samples in Louisiana, and various other work on his way to California to find himself working as ranch hand at a horse ranch.

But life on the road also has its twists and turns, like accidentally walking into a “Colored-Only” bar and having every eye in the place trained on the only white guy naive enough to set foot in the building. Smallwood describes his bike troubles, boarding houses, tin shack accommodations, speeding tickets, some difficult situations he got himself into and out of, and so much more that can happen on the open road. During his travels he met many characters, including some people who changed the course of his trip out of kindness, encouragement, and friendship.

Throughout his travels he would paint the names of the significant towns and cities he spent time in on the sides of his helmet.

Smallwood admits that any other mode of transportation just would not have been the same and that the little Honda 305 Super Hawk would define his trip just as his helmet defined where his travels took him. And yes, he still has the helmet. In fact, the helmet has travelled with him on European motorcycle trips, and he wore it while jumping out of an airplane a dozen or so times.

It’s an entertaining, easy-to-read coming-of-age story about an experience that changed a life, as only a motorcycle trip can do.

Dear Mom, Dad, Sis & Cat is available on for $22.82.

ISBN 9798360493389, 109 pages, black and white photos.


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