Indiana Daily Student

The 5,000 Mile Man

A glimpse at Winston Fiore life-changing trek

The 5,000 Mile Man
The 5,000 Mile Man

Sweat beaded upon Winston Fiore’s forehead.

It saturated his cargo shorts, T-shirt, and woolen socks. It clung to his skin as he neared the day’s roughly 25-mile mark after hours on foot.

As the IU grad walked along the highways, cars rushing past provided hints of breeze. On nights when he found $10-per-night hotels in Thailand, he dried his clothes over the air conditioner while he slept. He would wake the next morning to find his clothes wearable, but they would be stiff once the liquid evaporated, leaving only the salt lodged between fibers of synthetic fabric.

In the middle of Malaysia, though, hotels were too expensive. When the sun began to set, Winston set up camp. Finding a place to sleep was an art and a science — choose too open of an area and you risk being disturbed by law enforcement or passers-by.

Choose an area with too much cover and you forego the chance to enjoy the breeze.

Winston spent many nights with his two-man tent enshrouded by trees in oil palm plantations. All he wanted to do was sleep, but his body would not cool down from the day’s walk.

He lay there awake, sweat clinging to his skin.

Winston’s decision to spend a year exploring the world came to him in the back of a flatbed truck during the summer of 2007, as he was driving through stretches of Senegalese countryside.

Then 22, he had never traveled beyond the Western world. In Senegal, he witnessed women fetching water from distant sources and people dressed in rags rummaging through trash. It was so different from his middle-class upbringing in Bloomington.

His idea began to evolve — he didn’t just want to see the world. He wanted to interact with those living in it, as he had with the people during those three weeks in Senegal. He decided he would travel by foot instead of by car or airplane.

But he didn’t want to embark on his adventure without making a positive difference in the places he visited, so Winston began to search for a cause to attach to his journey. When Winston returned to Bloomington later that summer, he shared his plan with his parents even though the departure date was years down the road. He wanted to finish college, and that was about two or three years away.

“But to be fair, even at that point,” Winston says. “They were becoming used to my shenanigans.”

He hadn’t lived in one place for more than a year since he graduated from Bloomington High School North in 2003 — and still hasn’t to this day.

Straight out of high school, he served in AmeriCorps, followed by two years with the Marines, one year in New York City, one in Bloomington to attend IU, and another to study in Peru. He graduated from IU in 2009, and shortly after that, was deployed to Afghanistan with the Marines.

At the end of the summer in 2007, Winston moved to New York and received a newspaper article in the mail from his father, who had been keeping his eyes open for a cause for Winston to throw his weight behind. The article told of a non-profit group, the International Children’s Surgical Foundation, founded by a surgeon who performed cleft repair surgeries in developing countries.

“I read a piece about these guys,” Patrick Fiore wrote to his son. “It’s something you could look into.”

About one or two out of every 1,000 children is born with a cleft lip or palate, a developmental abnormality affecting a child’s mouth and palate. Without corrective surgery the fissure can affect the child’s ability to speak and smile.

The smile, Winston says, is at the very core of human interaction.

“To have that nipped at the bud is — it sucks. It’s not fair,” he says. “It’s not acceptable, and when the solution is so affordable and relatively quick, there’s no reason for children to be living like this.”

Winston adopted the International Children’s Surgical Foundation as a focal point for his journey.

In late September 2011, he set off on a 5,000-mile trek from Singapore, through Malaysia, Thailand, Laos and Vietnam, into China and Taiwan, through the Philippines and Brunei and back to Singapore.

He carried everything in nylon sacks attached to his tactical vest. The left pocket of his vest bore the web address he created for his journey, which he called “The Smile Trek.” Over a pocket on his right hand side, he carried a set of pictures of a girl before and after her cleft repair.

Winston spent 412 days walking the trek. He was alone most of the time.

Sometimes he played John Williams to make his journey seem more epic, but he quickly exhausted his music collection. Instead he downloaded public affairs talks, conversations, and interviews that allowed him to temporarily retreat into Western culture.

“You really — I don’t want to say drive yourself crazy — you seek out, as much as possible, conversation with other English-speakers,” he says.

Hearing conversations in his native tongue, even pre-recorded ones, felt rewarding. Outside major cities, in-person conversations with English-speakers were rare.

“It seems silly, looking back, like, ‘Oh, another Anglo. Let’s talk. You speak English, I speak English — let’s connect,’” Winston says.

There were the Westerners cross-country biking across Thailand. There was the French woman cycling through Laos. There was the group of white men riding Harley-Davidsons in Palawan, Philippines. And there were the American sailors in Malaysian Borneo where a naval fleet had docked.

“If we were to run into each other in Bloomington, we wouldn’t talk,” Winston says. “It’s because we’re outliers in whatever country that we have that connection.’”

But in Vietnam, China, and Taiwan, there was no one.

A pack of stray dogs barked hysterically as Winston, hovering at the 1,000-mile mark of the Smile Trek, chatted on the phone with a member of a Rotary Club.

Stray dogs regularly roamed the streets of  Thailand, and they often barked at Winston as he walked by.

The man on the other end of the line asked Winston if he was under attack.  

“I’m good, man,” Winston assured. “It’s just a bunch of — ”

A set of sharp teeth nipped at Winston’s right calf. He swung his umbrella at the dog’s face, but blood already pooled around the bite mark. The skin had been broken, and although Winston was about a mile away from his lodging for the night, he knew rabies was a concern. He stopped at a gas station, and the attendant doused the wound in disinfectant and iodine.

At the motel, a scooter taxi brought him to a nearby emergency room, where he received 11 shots — one in each shoulder and forearm, six in the wound on his leg, and one on his left buttock — just as a precaution.

The day started at 6 a.m. Any earlier, and Winston would have to pack up his gear in the dark.


He turned the screw on his inflatable mattress while still laying on top of it. His weight forced out the air. He sat up, stuffed his sleeping bag back into its sack, rolled up the mattress, dismantled the tent, and put on his vest.

Although each morning started basically the same way, the remainder of the day depended on his circumstances. If he was lucky enough to stay with a family inside their home, breakfast and electricity were usually available.

If not, he would walk until he found a place with food, coffee, and an outlet for his phone.

He would take breaks every couple of hours, ideally at a restaurant where he could eat, dry his feet, and change socks during the same stop. If there was nothing for miles, he would stop by the side of the road.

The best days were those in which he began his walks in the afternoons and continued until 11:30 p.m. That way, the sun beat down brutally for a few hours of the walk but most of the walking occurred past midday, accompanied by a cool and easy breeze. Those days occurred only when he could arrange the night’s lodging ahead of time. People aren’t too receptive to a man knocking on their door after dark, wearing what looks like a suicide vest and speaking a different language, Winston says.

Although he never went a night without finding somewhere to rest, finding a place to sleep was a constant source of anxiety.

The same year Winston graduated from IU with his degree in theater, he became disillusioned with acting. It wasn’t a burning passion, he realized. It was just a hobby.

“The moment I realized it wasn’t something that I couldn’t live without I said, ‘Well, I better stop now,’” he says.

He hasn’t acted since.

Somewhere in the middle of Vietnam in February 2012, a friend pulled out her laptop and showed him the documentary, “Dirt! The Movie.” A brief segment about homeowners growing grass on their roofs piqued his interest. He researched green roofs and came upon rooftop farming. “Why not use otherwise wasted space as a food source?” he thought.

Some Googling led him to The Urban Canopy in Chicago, a hydroponic rooftop farm just starting up. Within a week of watching the documentary, Winston got in touch with The Urban Canopy and made plans to work pro bono as an apprentice there.

Thirteen months after Winston found out about The Urban Canopy, he moved into an apartment on the south side of Chicago. He had a scheduled start date for the farm and a follow-up interview scheduled for a wait staff position at a local French restaurant. It was a relief, Winston says, to finally start his return to normalcy.

In some ways his experience was monotonous, Winston says. You wake up. You walk. You go to bed. Four months since the end of the trek, Winston catches himself looking back on the experience every now and again and is both overwhelmed and underwhelmed.

On one hand, he says, it’s difficult to think about the steps he took through the middle of nowhere. He has no regrets and would embark on another journey given the opportunity. On the other hand, it didn’t change him like he anticipated. He didn’t come back as a different person.

“The experience was very superficial in a lot of ways too because I never —”

He pauses to think.

“You can only connect with people and with a community so much when you’re just passing through.”

Grass crept onto the concrete porch in front of the house.

It was about 5:30 p.m., and Winston was about 25 miles from where his day began. He had digitally scouted out the area on his phone before he set out for the day. In the vast landscape of rural Malaysian Borneo, where only oil palm plantations interrupted the gaping areas of nothingness, it was one of the only ways to guarantee there would be a place to rest at the end of the day. Winston had marked a house, modest in size with a siding roof instead of shingles, as the first place he would try to stay for the night.

He knocked at the front door.

A man who appeared to be in his late-60s answered. He was shirtless and lean, possibly a farmer or fisherman, and unfamiliar with English.

Winston pantomimed: Looking for a place to sleep.

He motioned toward his tent, collapsed and attached to his vest, and pointed into the grass. Can I put my tent here?

The man, joined by his wife, motioned in return.

No, here. Inside.

The man and his wife showed Winston to the wash room, where he cleaned off before dinner. Afterward, Winston inflated his air mattress and unrolled his sleeping bag in the foyer, a large room furnished with a clothes line, two lawn chairs, and a box TV.

He fiddled around on his phone until he grew tired, checking his email and surfing the Internet. He ended many nights scrolling through his entire Facebook news feed until it started repeating itself from where it left off the night before.

It was a small way to feel connected to his other life, more than 9,000 miles away.

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