Can you remember what you were doing at five years old? Eating tubes of chapstick? Picking your nose? While you were busy writing on walls with markers, five-year-old Christian Thomas—a.k.a. Buddy Backpacker—was tackling a 2,180-mile hike. On January 20, 2014, Buddy, accompanied by his father Dion Pagonis, became the youngest person to hike the entire Appalachian Trail.

“We’ve always moved around a lot,” says Buddy’s mother Andrea Rego. “A normal life to Christian is traveling and not seeing the same people everyday. Dion and I are his home.”

The couple ditched their Long Island, N.Y., ties two years ago to head west. Buddy’s father Dion had been an Eagle Scout growing up and had tried to thru-hike the A.T. in 2011 but had to stop when he broke his ankle near North Carolina. Andrea, on the other hand, had never had any outdoor experiences but learned quickly under Dion’s guide. Together, the two took Christian to the mountains of Colorado, bouncing from Boulder to Crested Butte, where they currently reside.

“Christian is really open to new things and picks them up quickly,” Andrea says. “At the end of our last ski season, he was going down double black diamonds with no problem.”

The ski season is ultimately what drew the adventurous family to the Crested Butte area, but when they learned that the town shut down from April until June, Andrea and Dion started scheming plans for an off-season adventure.

“Once we started thinking about it and doing some research, we decided to try it for a month without the intention of finishing,” Andrea says.

To prepare for the hike, the family spent nearly the entire summer of 2012 in the Rockies. For one to two weeks at a time, Andrea and Dion would take Christian backpacking and expose him to the daily routine of a hiker. These forays into the backcountry were meant to test Christian’s ability to handle adversity and challenge, an experiment that confirmed to Christian’s parents that the decision to try the thru-hike was the right choice.

“Christian loved that summer,” Andrea said. “He would cry whenever we had to return to our apartment, so we would set our tent up in the living room to make him happy.”

When the family finally arrived on the East Coast to begin their adventure, day one proved to be one of the most challenging days of their nine-month journey. While driving to the Appalachian Trail Conservancy in Harpers Ferry, W.Va., the top on the family’s roof box flew open, littering the highway with all of their gear and supplies. It was pouring rain, and Andrea cringed as she watched car after car run over their things. In addition to starting off the hike with soggy, tread-marked gear, Andrea had also realized that she had left her wallet in Colorado, meaning the family would be hitting the trail without so much as a dime in their pockets.

“We told ourselves we’d make it through the rest of the trip so long as Christian was still having a good time,” Andrea says. “The first couple of days were definitely the worst, and it really tested our patience and whether or not we were going to be able to pull it off.”

For the first couple of weeks, Dion and Andrea juggled hiking with Christian and driving the family jeep to the next road crossing. Eventually, Andrea volunteered to sacrifice her chance to thru-hike and act as a support vehicle for the boys.

“This was never our hike,” Andrea says. “It was never my dream to do the whole thing but to help my family.”

While Dion hiked with Christian during the day, Andrea would drive to the nearest trailhead or road crossing, pack up the family’s meals, and hike in sometimes as much as 15 miles to meet up at that night’s designated campsite or shelter. Despite the rocky start, the family successfully summited Mount Katahdin after four months on the trail. After a two-week stint visiting family in New York, the trio headed back south in early October to their starting point at the A.T.C.

“We knew that even if we got to Georgia in December or January, the weather would be better than if we were in Virginia at the same time,” Andrea says, explaining their flip-flop hiking tactic.

The family, however, was unable to hike the Shenandoahs due to the government shutdown, forced instead to jump down the trail and finish the southern section before returning to Virginia in the dead of winter to wrap up the remaining mileage which was again put on hold due to snow. By the time they had reached the A.T.C. for the third and final time, they were excited but exhausted.

“The one thing we want Christian to take away from this is knowing that no matter what it is, he can absolutely do it,” says Andrea. “It takes time and dedication and patience and more patience. This type of life is a lot harder than having a normal day job. Sure, hiking the trail was like a vacation for nine months, but trust me when I say it has not been a walk in the park.”

Both Dion and Andrea ensured that Christian stayed up-to-speed with his schooling by giving him educational lessons to listen to while he hiked and a math workbook to use after dinnertime. They say the experiences he had on the trail taught him valuable life lessons like problem solving and perseverance, lessons he might not have been able to acquire in a traditional classroom setting. The family plans on returning to their home in Crested Butte for a while before returning to their adventure scheming.