It's safe to say that Dave Gill wasn't quite sure what to expect when he rode his bike in to Winnipeg. 

So how did the British blogger and film maker find himself falling in love with our province's capital? 

Two years ago, Gill was working an unfulfilling job in advertising. Although he’d had a successful career creating and directing television commercials, the daily grind of office chairs and stale coffee had begun to wear him down.

“I was at work, just looking out the window,” says Gill, “and I knew I couldn’t hack it much longer.”

So he did what many of us dream of, but few have the bravery or means to follow through with. He quit his job, grabbed a bicycle, and hit the road.

Dave Gill Route Map

Gill's journey will see him cycle nearly 12,000 miles throughout North America (Dave Gill)

“I left my job in England and flew to New York - with no prior cycling experience,” laughs Gill, “and I set off on 12,000 mile loop around North America.”

Gill arrived in Winnipeg with just over a month remaining in his journey. His year-long trek has taken him on a circuit around the United States, up the coast into Alaska, and across Western Canada.

But for Gill, the bike journey isn’t just a way to blow off steam. Rather, he’s looking at it as an opportunity to understand why people do what they do, and hopefully find some direction in his own life.  

“I was quite lost,” he admits, “so I wanted to speak to as many different people from many different backgrounds as I could - and ask them what they regret and what they’d do again.”

Cyclist Dave Gill in Manitoba

After nearly a year on the road, Gill hopes to end his journey and arrive in New York by the beginning of November. (Dave Gill)

Gill is documenting his journey through an online blog called Vague Direction, and posts interviews with the strangers he meets along the way. And although he still has another few weeks left in his journey, he says that the people he's met have profoundly influenced the way he looks at his own life. 

"The first few months I was still really cloudy," admits Gill, "but it's become clearer now - I've learned so much." 

The project will culminate in a “bicycle-powered documentary publishing project", that will be available as interactive e-book that incorporates video of the people he’s met on his journey.

In Winnipeg, he had the opportunity to sit down with local songstress Sierra Noble - and says he has been shocked by the city and the people he’s encountered here.

“It would be easy to just say this everywhere,” chuckles Gill, “but it’s my favourite city in Canada, without a doubt.”

"It's very warm and inviting - there's really no sort of intimidation here." 

If, at the end of his journey, he's still looking for his purpose and a place in life... who knows? Maybe he'll end up in Winnipeg.