He's always had wanderlust — at 15, he became obsessed with the idea of walking across Canada and begged friends to come with him. The plans fell apart, his friends grew up and they went to university or got full-time jobs.
St. Pierre felt stuck. At 21, he was spending his days answering phones in a FedEx office and crashing at home every night, drained of energy or inspiration.
"I went into a pit of depression. I couldn't sleep very well, getting up two or three times a night," he recalled. "I could hardly look people in the eye."
Then he came across an Internet forum thread about vagabonds. Intrigued, he clicked through and found Squat the Planet, an online community filled with tips on how to safely train hop, hitch rides or sleep outdoors. His old dream of travelling across Canada came roaring back.
One day, he asked his dad to drop him off at a truck stop. As St. Pierre got out of the car, all his father said was, "I don't know why you need to do this, but be safe."
His life as a hobo had begun.
St. Pierre is one of many young Canadians who are dropping out of the 9 to 5 life and hitting the road to work odd jobs, dumpster dive and sleep under the stars. But while vagabonds of generations past stayed connected through a secret code scratched on walls, today's hobos are turning to iPhones, Tumblr and Facebook.
"Never, ever, ever in our history have we been anti-technology," said Huck, a U.S. train hopper who asked that his real name not be used because his lifestyle is illegal.
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Huck is the founder of /r/vagabond, a reddit community for hobos to share photos and advice about living on the road. The forum has grown rapidly from 500 to 10,000 members in the past year, according to Huck, and has been featured in Newsweek and on the Vice Motherboard news website.
Many outsiders are surprised to learn that homeless travellers use the Internet and smart phones. But Huck pointed out that it's pretty cheap to buy a used cell and a small package of prepaid minutes. Even those who don't have phones can pop into a public library to use Google Maps or Craigslist, he said.
Jon Smith, a 16-year-old from Saint John, N.B., stumbled across /r/vagabond last fall while surfing the Internet. Amazed, he spent the harsh winter scouring the website and planning for his first big hitchhiking trip this summer.
"Here I saw an entire underground world of people I always thought of as bums, working together in a secret infrastructure in a seemingly solid and orderly fashion all over the world," he said in an email.
The demographics of online hobo communities are not easy to determine, as most people use pseudonyms and don't reveal much about their backgrounds. Both Smith and St. Pierre said they came from good homes, with loving parents and enough food on the table, although they were not rich.
Squat the Planet founder Matt Derrick said most members appear to be middle-class people choosing the lifestyle, as opposed to street homeless with mental health or addiction issues.
He added it's not clear whether the community is growing or if the Internet is just making it more visible.
"Some people travel for awhile and then they stop, have a kid and a family. People fall out of the community and people come in for the first time. Just like the culture itself, it's very transient," he said.
Vagabonds are also using the Internet to share and document their experiences. One Canadian man who goes by the name Wize Hop posts videos of himself hopping trains on YouTube, where they have been viewed tens of thousands of times.
Wize Hop, who asked that his real name not be used for safety reasons, said he began creating the videos to share his love of riding the rails, which he called meditative and therapeutic.
He's careful to post a disclaimer warning that train hopping is dangerous and illegal. While he's heard from some concerned viewers, he believes that overall his videos have a positive effect.
"I started to hear from people who wanted to break out of their shell, but felt it wasn't possible," he said. "So slowly it seemed like it wasn't just about the trains any more, it was about a greater concept of life, freedom, and what it meant to be true to yourself."
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