His days are filled with long stretches in the saddle, his nights are often spent camping under the stars. He doesn't know where he'll find his next meal or what's beyond the next curve in the road, but on his horse, headed south, Filipe Masetti Leite is truly content.

The Calgary-based cowboy has embarked on an epic 16,000-kilometre journey on horseback to his birthplace in Brazil — a trip he hopes will help him discover and highlight everyday stories of human kindness.

“People are just extraordinary. That’s what I wanted to prove through this trip and that’s what I’m experiencing,” the 26-year-old told The Canadian Press from a horse stable in San Acacia, New Mexico.

Sharing those experiences is a key part of Leite’s journey and it’s already clear that he is a long rider of the 21st century ­– blogs, tweets and short videos from the road convey snippets of his trip whenever cellphone service and the occasional Internet connection allows.

Despite having covered about 2,500 kilometres so far, he hasn't even hit the halfway mark yet — the entire endeavour is estimated to take him two years as he rides through 12 countries. But his tales from the trail are already bursting with episodes of adventure and anecdotes of discovery.

“It's been harder than I could have ever imagined but it's also been way more rewarding,” he says.

Leite, started thinking about his journey after graduating with a degree in journalism from Toronto's Ryerson University. The idea stemmed from a similar quest in 1925 by Aime Tschiffely, a Swiss school teacher who rode 16,000 kilometres alone from Buenos Aires to New York City.

Leite's father, an avid horseman who put his son in a saddle before the toddler could walk, always dreamt of going on a journey like Tschiffely's but was never able to.

“It’s kind of like I inherited this dream from my father,” says Leite. “I just had this overwhelming feeling that if I didn’t do this, I wouldn’t do anything else.”

After a series of unsuccessful pitches to sponsors, Leite secured the support of OutWildTV, a streaming television network focused on adventure travel and the environment. They now pay him a monthly stipend and will eventually turn his experiences into a documentary. A book and a reality television series could also follow, Leite says.

For now, though, his focus remains on the road.

A full day of riding typically sees him cover an average of 32 kilometres on trails, highways or open country. While he tries to take the most direct route, he often pauses to indulge in a new experience.

So far he’s taken a detour to participate in a Christmas parade, stayed longer in a small town so he could go bullriding and often, simply lingers at a resting point to swap tales with a fellow horse lover.

“I get to learn their stories in ways that I don’t think a lot of people get a chance to,” he says. “On horseback you see every pebble on the road and you get to really immerse yourself in the culture of the places you’re travelling through because you depend on people so much.”

That dependence is a very real part of his journey — Leite often relies on strangers for food and shelter. When he travels long stretches between towns though, it's just him and his three horses fending for themselves.

He recalls one challenging episode when, while crossing a mountain in the vast rural expanses of Wyoming, his supply of water ran out. The five-day climb over the peak was also the longest stretch he spent on the road alone.

“On the last night I had to give the horses oil,” he recalls, explaining that the animals required the liquid so their stomachs wouldn't seize up. “I ask so much of my horses so to not be able to offer the essentials is like a mother who can’t feed her kids.”

A different tense moment involved coming face-to-face with a bear who crossed his path, frightening his horses, but ultimately causing no harm.

Leite anticipates, however, that the most dangerous part of his journey will come next month when he crosses the U.S. border into Mexico.

The country’s war on drugs has resulted in a perilous security situation, and has prompted Leite to consider travelling through certain stretches in a horse trailer.

“It’s no joke,” he says. “Northern Mexico is going to be about keeping myself and the horses alive.”

Ultimately though, the cowboy is focusing on the long-term positives of the year and a half of travel he still has before him. “I love travelling because you get to learn so much,” he says. “The lesson that I’ve learned the most is how kind and loving people are and I think that’s something that I’m going to talk about for the rest of my life.”

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