My Trans-Canada Bike Adventure—Winnipeg Edition of the Ride for Di

47 Years Ago, Winnipeg Changed My Life

In an earlier blog, I reflected on the fun double meaning of calling this the “Journey of My Life.”

First, this is the biggest physical challenge I have ever taken on—and probably ever will.

But there’s the other—this journey is roughly 7,000 kilometres long, and I’m 70 years old. That means I can map the ride against my life:

Every 100 kilometres represents one year.

As I pedal along, I find myself thinking about those 100-kilometre markers and asking: Where was I at that age? What was happening in my life?

Sometimes the parallels are quite funny..

A Shitty Day for a Shitty Year

Day 20 was a shitty day on the bike.

The rain was pounding on my tent before I even got up and persisted for much of the day, finally stopping shortly before I rode into Portage la Prairie. Add the cold and a strong, unfavourable headwind, and it was easily the worst riding day of the trip so far.

At the start of that day, I had reached 2,163 kilometres—the equivalent of being 21 years old in the “Journey of My Life.”

So what happened when I was 21?

My father died, and a seven-year relationship with my high-school sweetheart ended.

A very shitty year for the first reason. In retrospect, considerably better news on the second.

So, yes, the shitty cycling day more or less lined up.

Day 21 was different. Dark, low clouds threatened rain all day, but they produced only a couple of hours of drizzle. Better still, the crosswinds turned favourable, and what could have been another grinding day became a surprisingly easy recovery ride.

On the road to Winnipeg.

A recovery year, perhaps?

By the time I reached Winnipeg, my bike computer showed I reached 2,381 kilometres.

Twenty-three years old in the “Journey of My Life

Dear reader, you might ask, “What was significant in your 23rd year?”

For a start, on Saturday, August 11, 1979, I was in Winnipeg.

I was a University of Waterloo co-op student on a work term with a publishing company. They had sent me on a mission to visit major independent booksellers in Northern Ontario, Winnipeg, Regina and Saskatoon.

Armed with my book bags—large, hardened suitcases filled with sample books—I met with store buyers and showed them the hot titles for the coming season.

You know, the really exciting stuff.

Like the latest edition of Edna Staebler’s Food That Really Schmecks.

Who could forget?

As I travelled through Northern Ontario, I took lots of photographs with my old Nikon FM 35mm SLR. By the time I reached Winnipeg, I had five rolls of 36-exposure film that I desperately wanted developed.

For anyone who grew up with digital photography, it’s hard to explain the suspense involved in taking pictures back then. You could spend days happily clicking away without having the slightest idea whether you had captured a masterpiece—or 180 badly exposed pictures of your thumb.

So when I arrived at my Winnipeg hotel around 3:00 that Saturday afternoon, finding a photo shop was urgent. In those ancient times, stores closed early on Saturdays and stayed closed all day Sunday.

From my hotel room on the 21st floor, I spotted a store below and figured out how to reach it. I would have to cross a major intersection about a block away.

The corner of Portage and Main.

How did I not know about this famous intersection?.

I was 23. I was a kid. I was naive. And I wasn’t particularly worldly.

I was almost at the store when two young women crossed the street and stopped me.

“Can you tell us how to get to Portage and Main?”

I laughed.

I explained that I had just arrived in Winnipeg myself and that, by sheer coincidence, Portage and Main was the only intersection in the entire city I could actually help them find.

They laughed too.

They had just arrived from Vancouver that afternoon and were in Winnipeg for a two-week session with the Royal Winnipeg Ballet.

As naive as I was, I thought dancing with the Royal Winnipeg Ballet sounded pretty amazing.

I would run into them twice more on Sunday before finally asking them to join me for a drink in the hotel bar.

In those days, Winnipeg bars couldn’t serve you just a drink on the Sabbath. You had to order food as well.

One of the women ordered a Brown Cow—Baileys Irish Cream and milk—along with french fries and gravy.

An unforgettable culinary combination.

Hey, we were 23.

And that woman would become the love of my life.

The Road Ahead

Winnipeg changed that 23-year-old forever.

Today, 47 years later, I have roughly 4,700 kilometres of road still ahead of me. But this time I have maps, apps and a reasonably good idea of the hills, turns and obstacles that lie between Winnipeg and the Atlantic.

That 23-year-old had no such map.

He had no idea what lay ahead over the next 47 years—the heartbreaks and losses, certainly, but also more happiness than he could possibly have imagined.

He didn’t know that the young woman drinking a Brown Cow and eating french fries with gravy would become his wife.

He didn’t know they would raise two wonderful children, welcome a daughter-in-law and son-in-law into the family, and eventually find themselves surrounded by four beautiful grandchildren.

He didn’t know any of it.

Which, perhaps, is just as well.

At 23, the road ahead seemed almost endless.

At 70, I know better.

On Day 21, I road to the intersection of Portage and Main and found that all my wonderful memories of around there have been paved over with time.

Roads have a way of disappearing beneath your wheels much faster than you expect.

And so do years.

He would be shocked to know how quickly 23 years of age becomes 70.

And somehow, 47 years after a chance encounter with two strangers asking directions at Portage and Main, I have pedalled my way back to the very place where the most important journey of my life really began.

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4familyfriends

I write about the small and significant moments that shape our lives — family stories, friendships, personal observations, lessons learned, and the quiet experiences that often matter most. This site is a place to reflect on life with curiosity, gratitude, and honesty: the challenges that strengthen us, the people who influence us, and the everyday moments that deserve to be remembered. From cycling journeys and travel to conversations with grandchildren and reflections on resilience, I hope these writings encourage thoughtful living and deeper connection. My mission is to build a family legacy of strength, generosity, and steady & trustworthy leadership — embracing physical challenges, growing continuously, and encouraging my family and community to rise to theirs. I believe a meaningful life is built not only through accomplishments, but through consistency, kindness, endurance, and the example we leave for others.

5 thoughts on “My Trans-Canada Bike Adventure—Winnipeg Edition of the Ride for Di”

  1. Sweet. Arriving in Winnipeg was extra special.
    Keep riding strong Barry!
    Birotavi, vidi, vici — I cycled, I saw, I conquered.

  2. What a great story! I had never heard how you met your wife, it’s an even better story than me picking up Shirley hitchhiking. I love that sometimes different languages have words that don’t exist in our own tongue. There is a Japanese word, goen, which as I understand it, embodies the luck, fate, and faith required to bring exactly the right person into your life at exactly the right moment. Goen was clearly working for you on Saturday, August 11, 1979. Your recall for specific dates is FAR superior to mine, but it must have been right around the same time that I picked Shirley up off the side of the road in Ottawa. More Goen in action:).

    1. Whether due to memory or a journal, you do still have much better records of the distant past than I do :).

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