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

Headwinds, Cold Mornings, Warm People

Today I crawled into a campground just east of Brandon, Manitoba, after a day of unrelenting headwinds and crosswinds.

So far, I’ve travelled more than 2,100 kilometres—about 30% of this journey of a lifetime. My legs are suggesting that 30% is a much bigger number than it sounds.

I have no idea how many pedal strokes that represents. But, as I mentioned in an earlier post, every turn of the crank moves me in three directions: physically, toward St. John’s; inwardly, along a path of reflection about what’s possible at this stage of my life; and outwardly, toward honouring my sister Dianne by raising awareness and funds in the fight against ovarian cancer.

Learning, Earning, Returning

There’s a popular idea that life can be divided into three stages: learning, earning and returning.

I’m relatively new to the “returning” phase, having retired only a few years ago. Part of this ride is figuring out what that means.

What can I still contribute? How can I make a difference to my family, friends and community? And what constraints of the “earning” years am I finally free of, allowing me to do things differently?

Not long after leaving Mile Zero in Victoria, I received a message from an old friend, Mike, who lives in Calgary. He invited me to stay with him when I came through town.

I hadn’t seen—or even talked to—him in years.

But Mike isn’t just an old friend. He’s a really old friend. Our friendship goes back 45 years, to when we were young guys working together at a publishing company in Vancouver.

He was Best Man at my wedding.

When I arrived in Calgary, I discovered that Mike has barely aged. He’s still tall, fit and handsome, with a full head of hair—all qualities a guy like me could easily hate. And although he’s a couple of years older than I am, he isn’t quite retired yet.

Fortunately, he’s also an extraordinarily good man.

Mike went well out of his way to help me sort out bike shops, replacement parts and the assorted mechanical crises that come with dragging a heavily loaded bicycle across Canada.

He and his wife, Caroline, live in a beautiful, walkable neighbourhood. Soon after I arrived, Mike took me for a stroll. We picked up fresh buns from a nearby bakery and ice cream from a local creamery.

That evening we feasted on hamburgers made with great Alberta beef, followed by homemade blueberry crumble buried under ice cream. Joining us were Mike and Caroline’s daughter and her boyfriend, both in their twenties and already building solid careers with large companies—an impressive start to their “earning” years.

The conversation left me feeling pretty good about the future when it’s in the hands of young people like them.

The next morning, Caroline made me a huge breakfast and sent me off with a homemade sandwich. Mike got on his bike and rode with me through Calgary, making sure I found the pathway that would take me safely out of the city and eastward again.

Mike showed me a Calgary like I’ve never seen before. Here people are drifting at 7kph (I matched my bike to their speed) on the turquoise water of the Bow River. People are laughing, playing music…Life is Good.

Then I was on my own.

And somewhere out there on the road, with Saskatchewan ahead and far too much time to think, one question kept bothering me:

Why the hell did I ever let this friendship go quiet?

Too busy earning?

Too busy with life?

Too confident there would always be more time?

One thing this ride is teaching me is that “returning” doesn’t have to mean only giving something back to the world.

Sometimes it means returning to the people who mattered along the way.

So I’m making a list.

Old friends I haven’t called.

People I’ve lost touch with.

Friendships worth recovering.

I still have thousands of kilometres ahead of me.

Apparently, I also have a lot of phone calls to make.

After a Hot Day in the Saddle

At a campground in Bassano, Alberta, a guy named Curtis walked up to my picnic table.

He had a biker beard—maybe four inches wide and twice as long—a T-shirt, jeans and plenty of tattoos on weathered, tanned skin. He looked like a guy who either works outdoors all day or rides his chopper all day. Possibly both.

He was about the right age to be a “returning” kind of guy.

He had come over from his RV, where he had parked his motorcycle—a chopper with bizarrely high ape-hanger handlebars, straight out of the 1969 classic Easy Rider. He also had a sports car which, when he started it at 5:30 the next morning, produced roughly the same amount of noise as a jumbo jet at takeoff.

Curtis handed me Popsicles, a Pepsi and a bottle of water.

Then he plopped down a glass full of ice and started pouring Jack Daniel’s into it.

“Say when,” he said.

“When, when, when, when…WHEN”

Apparently, “when” means something different in Alberta.

What an impressive “home” pour.

And what a wonderful, completely unexpected act of generosity.

RVs in Alberta—and Returning

In Medicine Hat, the campground, like most I’d seen in Alberta, catered mainly to RVs. But this one had two tiny, side-by-side “Bike and Tent” campsites—just enough room for a tent, with no space for a car, let alone a house on wheels.

While I was eating my freeze-dried dinner at the picnic table, a man rode his motorcycle into the other site and set up camp.

Later, he walked over carrying two cans of beer and plopped one down in front of me.

That beer turned into a long evening of conversation between two men firmly planted in the “returning” stage.

Gerald—or Geri, as his friends call him—is from New Zealand. He’s 67, fit and energetic. He was riding from Alaska to the southernmost reaches of South America.

He described seeing elk, caribou, bison and some of the most spectacular scenery imaginable. He was travelling with little more than what he could strap onto his motorcycle. He’d already done similar trips through Asia and plans to tackle Europe and other parts of the world.

Across the road from us sat an enormous RV, roughly the size of a Greyhound bus, complete with slide-out compartments and a small car being towed behind it.

Geri looked over at it.

“Everyone wants to get away and leave it all behind,” he said. “These people want to get away and take everything with them!”

Freezing cold mornings…Darth Vader at the picnic table.

I laughed.

But it also left me thinking.

How much stuff do we really need?

And how much of this “outdoor” living do I want to do in the last stage of my life?

Geri seemed to have answered that question for himself.

Everything he needed was strapped to a motorcycle.

Salt of the Earth

On Sunday night, I ended up in Chaplin, Saskatchewan—population 222.

After a tough week of riding, I decided to treat myself to a proper Sunday dinner at the town’s only bar and restaurant.

So much for a Sunday dinner. Pub Grub was all that was on the menu.

I was the only customer until I was about halfway through my meal.

Then five people came in and sat at a round table beside mine. Suddenly, I felt like an imposter, someone who stumbled in and sat down in their dining room.

They were wonderfully friendly—and wonderfully curious about the alien, me, who had invaded their home turf and the even more, about the alien thing I was doing: riding a bicycle across Canada.

When I went to the cashier to pay, one of the men got up and walked toward me.

He was a giant of a man—big, strong, and wearing clothes that looked as though he’d been working in them all day. He looked to be in his sixties.

He introduced himself as Tex.

He told me he’d been born in Chaplin and had worked the family farm there all his life.

Then he pointed toward the table.

“That’s my dad over there. He’s ninety.”

He paused.

“People here are good.”

I grew up in the country, and it occurred to me that farmers never really retire. They just keep working, helping and contributing for as long as they can.

Tex put his massive hand on my shoulder.

“My mom died some years ago from breast cancer,” he said. “I like what you’re doing.”

His eyes got a little watery.

So did mine.

Then he said:

“I got your dinner.”

And suddenly my disappointing Sunday pub grub was something so much more impactful…

Maybe farmers don’t have three stages of life..

Maybe, for people like Tex, returning is simply something they do all their lives.

Salt of the earth.

And out here on the Prairies, I’m discovering there’s an awful lot of it

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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.

3 thoughts on “My Trans-Canada Bike Adventure — Prairie Edition of Ride for Di”

  1. What a thoughtful, reflective, and poignant post. Like you, I am in the returning stage. And like you, I’ve been reaching out to old friends reconnecting threads of our lives. So glad John and I were able to have dinner with you and Deanna in Ottawa last spring. Hopefully we can have dinner when (if) you pass by our neck of the woods in Ontario. We’ll even bike with you for a while.

    1. Thank you, Shirley! I’ve been so terrible in keeping in contact with great people like you and John. I look forward to meeting you sometime soon—and on a bike would be perfect!

  2. I remember you being so surprised when you and I were getting ready for a squash game at U of S in Saskatoon decades ago. Having forgotten my racket, I asked the guys that were finishing up in the court we were about to use if I could borrow one of theirs, and I was handed one of their rackets without hesitation. From your stories, it seems some things about Saskatchewan haven’t changed :).

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