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Wandering from Winnipeg

  • Aug 29, 2016
  • 4 min read

The bus is rolling down Portage Avenue when I feel a tap on my left arm. Turning, I am met by a small elderly woman wearing polka dots.

"Are you a traveler?" she asks, her eyes rich with excitement and curiosity.

I share my journey thus far and my plans for hitchhiking from Winnipeg to Vancouver.

"Ooooh, exciting. Have you had wonderful experiences so far?"

We smile at each other and I feel a kinship. She frantically scribbles her granddaughter's contact information on one of the many receipts cluttering my wallet.

"She lives on Vancouver Island, it's a very spiritual place. The trees are magical there. She would love to meet you"

Despite the bus having passed her stop, she has stayed on to point out the best spot for me to hitchhike from. When we reach Charles Street, I shake her hand and she warmly grasps mine in hers.

"What's your name dear? I'll tell her you're coming, and I'll put you in my prayers. Safe travels"

Walking down the Trans Canadian highway, I can't help but beam as I reflect on our exchange. As far as omens go, you can't beat the blessings of an elderly woman. Especially when the word hitchhiking is mentioned. A word that brings fear into the hearts of mothers and grandmothers everywhere. I notice a swarm of crickets following me. They leap and jump across my path. All nerves I have begin to vanish. I breathe deeply. This is the third time I am hitchhiking by myself. The first was due to circumstance. I'd missed the bus back to Edinburgh from Dunfermline after a Belle and Sebastian concert and had no choice but to hitchhike. The second was from Mount Vernon to Seattle - a meager 2 hour journey compared to the week long adventure I was about to embark on.

I walk to the perfect hitching spot. It has a wide shoulder, is before a traffic light, next to a Tim Horton's and right after a connecting highway. I tug the sign for Brandon from my backpack where it sits among a selection of handmade signs on dollar store cardboard. All for small Prairie towns I will be visiting over the next few days.

I move my backpack and sleeping bag to just off the road, smile and within minutes a truck pulls over. I struggle to lift my backpack above my head and onto the passengers seat but with a little help, we are off! My third time solo hitching.

My driver is James. He offers me a cigarette and a lift to Regina and we begin to chat. He is 49. Originally from Toronto, he moved to Winnipeg in his twenties and has lived there ever since. He has driven trucks for 24 years and his profession has seen him drive across Canada and the United States. His trailer has dog food and his final destination will be Lethbridge, BC. He loves his job. Every day is different and through his line of work, he has seen every U.S state and every Canadian province. He was a professional ice hockey player for the Toronto Maple Leaves until a shattered knee destroyed his career. He was married, but divorced after he caught his wife in bed with another man. They have a 14 year old son together whose birthday is next week. James is getting married again. He met a woman through facebook and next year they will be getting married in the Philippines.

I grill him about truck driving. I've hitched with truck drivers before in Europe but the language barrier saw my questions unanswered. Does he recognise truck drivers at regular rest stops? Yes, but only the terrible drivers.

Are there many female truck drivers? Yes, in fact his ex-wife was a driver. Has he been to the Yukon before?

Yes, but he would never go again. Same case with Alaska. He lost a buddy of his to the dangerous ice roads up there. "I got him into truck driving. We went to school together and he wanted to get into it. I took him along with me in my truck one day and taught him everything I know" "I'm sorry to hear that, man" "It's okay, he was a dick anyway"

Does he pick up hitchhikers often?

In the last 24 years, I am the third he has picked up. A buddy of his was killed by a hitchhiker who stole his truck. I am shocked and our conversation falls silent. I am reminded of how dangerous hitchhiking can be for both driver and hitcher. He breaks the silence. He recalls a story of a heavily pregnant woman he picked up hitching from Alberta to Manitoba. It was Winter. Despite his buddy, he always makes efforts to pick up women. "I can't let the wrong person pick them up. I'm not a scumbag"

He shares his knowledge of the Winnipeg area. He claims it is the tallest point in Canada. I argue that the Rockies must be, but he assures me it is Winnipeg. He tells me about an underground subway system built over 20 years ago that has never been used. I don't know whether to believe him or not but the enthusiasm and excitement of sharing his home is outstanding.

He tells me about the weird things he's seen whilst driving.

Lots of accidents. It seems like every 20km along the Trans-Canadian to Brandon, there has been a death at the hands of a drunk driver. He has driven through tornadoes so strong he felt his entire truck shake and the doors only just resist gale force winds.

"One thing a lot of people don't realise is that truck drivers can see EVERYTHING" Blow jobs, people getting changed, nudist drivers. He's seen it all.

As we roll along the highway in comfortable silence, I'm truly in the heart of the prairies. It begins to rain and I am grateful for the warmth and shelter of the truck. I am dropped at the outskirts of Brandon on the trans-Canadian highway - a highway I will be more than familiar with over the next couple of months. I wave James goodbye and consider the possibility of getting a lift with him on my way back to Winnipeg. As I wait outside the gas station for my couch surfing host, I exchange a smile with a young motorcycle rider. The kinship of the alternative traveler.

A young woman my age passes me, she takes one look at my backpack and signs. "Be careful"

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