Boy Meets Wild

After 35 years, David Winter recalls what it was like to take on the Long Trail at age 14

Story and photos by Jenna Burleigh

Staring down the darkening path before him, he feels a bit overwhelmed, unwelcome. He ventures one step, and then another. Just 272 miles to go for 14-year-old soloist David Winter as he embarks upon the Long Trail, Vermont’s longest, most arduous hike.

“It’s getting late, and this forest doesn’t look like anything I know,” Winter recalls thinking during his first night on the trail. He was alone, no comfort provided by reassuring footsteps beside his. “The awareness of an entire month out there kind of set in and bothered me a little bit that night,” Winter says.

"It didn’t look familiar to me. It was different. I didn’t feel at home."

At that time, Winter was the youngest solo hiker to take on the Long Trail. It would have been unlikely for him to undergo this feat without the slightest sense of unease. “It didn’t look familiar to me. It was different. I didn’t feel at home.”

After his tentative start, he went on with a certain fondness for the outdoors. “Within a couple days I was so happy to be out there,” he says.

Winter set out on the Long Trail on July 16, 1974. It was more than a month later, on Aug. 26, when he took his final steps on the hike and completed his end-to-end journey.

Thirty-five years later, a baseball cap balanced atop his head, sporting a wispy mustache and blond pony-tail, Winter sips his coffee, wearing the face of a man who has conquered one of Vermont’s wildest challenges. He laughs as he recalls certain points of his journey, remarking on how young he really was.

“When I was a kid, we spent quite a bit of time hiking,” Winter says. He used to camp with his family, and it was on one such trip that he decided to go out on his own. Winter spent a few nights by himself on Mt. Mansfield’s summit, and his expedition that weekend formulated into the desire to hike the Long Trail.

Perhaps it was a wild idea at the time, but Winter was brave enough to try it. “I don’t know, it was just one of those things,” he says.

The Long Trail is the creation of James P. Taylor, who once said the intention of the trail was to “make the Vermont mountains play a larger part in the life of the people,” as stated on greenmountainclub.org. The beginnings of the Long Trail and establishment of the Green Mountain Club are synonymous. The GMC has been maintaining and protecting the trail since its completion in 1930. The 272-mile trail blazes along the spine of the green mountains, stretching from Massachusetts to Quebec.

"For somebody 14-years-old, it was a little bit involved."

The GMC maintains the trail by “mak[ing] the trail more sustainable and durable,” says Ned Houston, information specialist at the GMC visitors’ center. This includes the “clearing of brush and blow-downs,” clearing muddy or wet areas, and adding stone where necessary to stabilize the trail.

Houston says the trail is maintained by a “huge contingent of volunteers,” as well as what is called the “Long Trail Patrol.” These individuals work to keep the trail clear of obstructions and make it as easy to maneuver as possible.

“For somebody 14-years-old, it was a little bit involved,” Winter says.

After much planning, and weeks of preparation, Winter was finally ready to set out on the adventure of a lifetime. He grabbed his pack filled with a sleeping bag, mess kit, pocket knife and cooking stove, nothing more than the essentials. Adjusting the straps around his shoulders, the 14-year-old took his first steps down a long, long road.

Launching his journey at the Vermont-Massachusetts border, Winter started up the trail, which rose slowly into the mountains, affording a short hike to the first shelter. There are more than 70 shelters along the trail; some are cabins, but many are lean-to’s. “You can pretty much count on a shelter being available within a day’s hike just about anywhere on the Long trail,” he says.

Though Winter says he was never left out in the rain, there were a few nights the shelters were fairly cramped.

Yet his first experience with Long Trail shelters was anything but crowded. Winter spent his first night alone in a lean-to. “The first day I felt a little bit homesick,” Winter says.

As time went on, those feelings melted away. “Within a couple days I was so happy to be out there,” he says.

Though Winter may have overcome his homesickness, home surely missed him.

Hazel Winter says she missed her son very much, but she knew he would be alright. “He’d had a lot of experience in hiking and camping,” she says. “It was something he was quite familiar with.”

As planned, every four to seven days Winter’s parents would meet him at certain “food drop” points. “It was all pre-planned,” Hazel says. “He knew what he wanted.”

There was one day Winter was late to his drop point. “We had not figured some of the difficulties,” Hazel says. The terrain was a bit steeper than expected, and the hike was more strenuous than previously thought.

Winter’s parents would provide their son with food at these “food drops,” always making sure he was writing in his journal each night.

In order to be a validated “end-to-ender,” the GMC requires a hiker to submit a journal, a synopsis of their journey. Once the GMC has approved the journal, a hiker receives a GMC patch, and an “end-to-end” patch, along with a certificate.

However, to get the patches, a hiker must make it all the way to the end, which is quite a feat for even the best-behaved hikers.

"I had a 12-hour hike that day to be on time for the following day."

At 14 years old, Winter had an inclination toward trouble. “Just north of Rutland, I met two guys,” he says; that’s how the story begins. Boys will be boys, as they say, and Winter was in for a long night. Needless to say, Winter wasn’t waking up too early the next morning, which proved to be his longest day on the trail. “I had a 12-hour hike that day to be on time for the following day.”

“I didn’t make it as far as I had planned,” Winter says. In order to be at the right spot at the right time, he had 17 miles to hike. When he finally made it to the shelter, Winter recalls forgoing dinner for sleep, crawling into his sleeping bag as soon as he arrived.

Although Winter faced a few self-induced hardships on his trek, he never really met much danger. “I came across a Vietnam vet who was working out some of his memories, but that was about it.” Winter eventually found it was he, himself, who stood in the way of the finish line.

Winter started to feel a bit unlike himself. His muscles ached and chills raced through his body. “I ended up getting really sick 11 miles from the Canadian border, just South of Jay Peak.” Unable to carry on by himself, Winter was lucky to meet a Canadian hiker who took him to the Jay Peak ski area. “I was so feverish I wouldn’t have found it,” he says.

Due to his illness, Winter had to put the trail on hold.

But stubborn, as his mother would say he is, Winter was determined to finish what he had started. He went home to regain his health, and returned three weeks later with a friend to complete it. He submitted his journal and received his patches, the priceless objects the 14-year-old Winter had been so eager to attain.

Even 35 years later, Winter recalls the greatest aspect of it all was “just being out there.”

“I think I took away from it a sense of independence, a sense of accomplishment,” Winter says, readjusting his baseball cap. “Just having done it, just having had the experience, regardless of what anybody else has done, is, in itself, the whole point.”

Winter would like to take on the mighty Long Trail once more, but doubts he ever will, joking that “It would be a good way to quit smoking cigarettes.” On a more serious note, Winter says, “I’d like to do it again, but it would be a bit of a process to get myself back in shape to consider it.”

These days, Winter says he goes for day hikes, but doesn’t do much overnight hiking. Though he doesn’t spend so much time on the mountains anymore, he can’t forget what it felt like to pack his things and spend the summer hiking along Vermont’s famous peaks.  Sipping his coffee, he remembers being young, adventurous, and wild. He climbs into those memories and recalls what it was like to be a boy.

Looking back, he smiles. The trail fades away from the soles of his feet as he slips his arms through the straps of his pack, unloading the weight he had carried so far. Winter walks away, an overwhelming sense of pride and accomplishment filling his entire being. Turning back to steal one last glance at the wilderness that had quickly become a part of him, Winter’s journey was finally over.

Have you ever hiked the Long Trail or any of the side trails?