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Portland to New York City in 56 Days

Isabelle Gobbi

Dobrindt during his trip.

Photo courtesy of Emerson Dobrindt.

From the rolling green hills of the Pacific Northwest to the steep peaks of the Appalachians, senior Emerson Dobrindt spent his summer discovering America’s vast and diverse landscapes. Over a period of 56 days, he biked 3,800 miles from coast to coast. 


Dobrindt, who knew since last year that he wanted to make his summer a “big trip,” struggled to find the perfect expedition. After researching different possibilities, he and his family settled on an organization called Teen Treks, an educational travel program that offers various bike trips for adolescents. 


This discovery was perfect for Dobrindt, who has a passion for cycling. “I have a lot of experience in biking,” he said. “I race in triathlons, I do biking races… I’ve been interested in biking all my life. I work in a bike shop. It’s something I truly enjoy.” 


On Tuesday, June 27, Dobrindt arrived in Portland Oregon, where his adventure would begin. He and six other teenagers–as well as two adult chaperons–were ready for their trek. 


Each cyclist had their own road bikes and carried their essentials in their backpacks. In his, Dobrindt had four pairs of clothing, the tools needed in case of mechanical problems, some food, and dispersed group gear. 


As a self-sufficient group, the cyclists had no car and cooked their meals with food purchased that morning. Besides their six rest days, when they spent the night in hotels, Dobrindt and his companions camped every night. 


In the beginning, Dobrindt felt he had gotten into something bigger than he had anticipated. “I was struggling the first week,” he said, “but overall I got stronger and stronger and feel much better than I did when I started, so I’m happy about that.” 


Beyond the physical effort, there was also an important spiritual dimension to Dobrindt’s trip. He explained, “Sure the trip is big physically, but it’s also big mentally. You’re on a bike for eight hours a day, and there are times you are sitting with your thoughts for hours on end.” This was tiring, he said. “We had days that felt long. I think that was our biggest struggle.”


Throughout their journey, the cyclists became very close. Today, Dobrindt considers them like a second family. 


As the weeks went by, the cyclists experienced the kindness of strangers. Every day, the group would be asked about their said. “We’ve had a lot. ...of people give us food or drinks, or a place to rest.”


The most memorable stranger was Joe Young, a man the teenagers met in Great Falls, Montana. “He offered to let us stay at his house and cook dinner and breakfast for us. He was very kind and generous enough to let us stay there,” Dobrindt recounts. “We were really excited because we don’t get to have experiences like that often.” 


After Montana, which was mostly wheat farms that stretched “miles on end,” the cyclists arrived in North Dakota, where they biked 400 miles on an interstate. 


On Wednesday, August 16, the trekkers arrived in New York City. They had crossed 13 states, overcoming mechanical issues, wildfire smoke in the Northwest, and persistent rain in the Appalachians. 


According to Dobrindt, adjusting back to their normal lives wasn’t easy. The trip felt never ending, so “it felt weird to not be riding every single day,” he explained. 


Dobrindt hopes to pursue a career in cycling. He would love to discover more parts of the world with his new family of cyclists. 


Throughout his journey, Dobrindt met many kind and thoughtful strangers from around the country, showing him how generous people can be. He said, “Most people see the world as a bad place, but if you look in these small communities you’ll find kindness. There are people out there who would love to support you through your journey.”  


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