Former teacher finds new adventure as sailing instructor

It’s always interesting to see and talk to GHS grads who have “taken a turn” from where we know they have been since leaving GHS and our small town.
For instance, Jared Collingwood, son of Dave and Vickie Collingwood, has been a Spanish teacher and coach for going on 14 years.
We knew he and his wife Patricia were always looking for adventure, looking for new places to live...and that he had taught in Greybull, Riverside and, in 2015, accepted a job in Cheyenne.
But until a year ago, when Dave attended a basketball game in Wright with us, we had lost touch with him.
We discovered Jared, Patricia and their sons Lucas, soon to turn 12, and Matias, 7, were living in Massachusetts and loving it. He was still teaching Spanish, but to fourth- and fifth-grade students; in fact, he is in his fifth year. Teaching at the primary level was a switch, but he enjoyed it immensely, although he admitted he missed the “mentoring and interaction with the high school teenagers.”
His tenure there coincided with the pandemic. It was a difficult time financially as America struggled with businesses being temporarily closed, school closures, etc. So Jared went looking for a summer job, something to augment his income.
He obtained a job working at a yacht club, teaching sailing to boys and girls ages five to 18. He accepted the job, and the challenge, though he had a lot to learn himself.
How did a young man from a small town in land-locked Wyoming end up teaching sailing in Massachusetts?
Jared shared his story.
For a little background, Jared was born, raised, educated and graduated from Greybull High School, earned his college degree and returned home to teach Spanish and coach at GHS for three years. He married Patricia, a native of Lima, Peru, in 2007.
After his three-year stint at GHS, Jared and Patty wanted more “adventure,” something different.
“We decided to move to Peru to experience my wife’s home country and life for a while,” he said. They returned to the U.S. a year later. “We lived in New Jersey with Patty’s cousin during this transition period,” Jared said.
During the transition period, Jared worked part-time on the East Coast until he secured a position as a Spanish teacher at Central High in Cheyenne. The family loved their life in Cheyenne. It was near Fort Collins and Denver; there were lots of things to see and adventures to be had. But when their youngest was born, they felt it would be beneficial to be closer to family for some support.
So the Collingwoods moved back to the Big Horn Basin to teach at Riverside in Basin. Jared taught high school Spanish and took a position as the head basketball and track coach. Coaching, Jared shared, was “really what I wanted to do.”
But already the family was planning new adventures. Patty had been longing for a return to the water. “We thought about a job overseas, maybe in Europe. We want to experience that someday,” Jared said. It remains on their bucket list.
In the meantime, they landed in Duxbury, purchased a home and settled in.
Then COVID hit, and times became tough. Jared began his search for a good-paying summer job. Through a set of circumstances, he heard that the Duxbury Yacht Club was looking for a director to head its Junior Sailing program and learned the name of the man to contact.
As it turned out, Jared had taught the man’s son, and Lucas and his son were friends. Jared messaged the man and admitted that he did not have any qualifications, but he did have experience coaching and running athletic programs and was willing to learn. Imagine his surprise when he landed an interview and “was lucky to be offered the job.”
“I still have a lot to learn, but it is a ton of fun and I get to spend almost the entire summer on our beautiful bay and travel to other local areas, like Cape Cod, helping kids have fun and race sailboats. I am exclusively working with kids five to 18 which is right up my alley.”
He explained the different “sailboats” they practice on, starting with those used by the youngest and then those used as they grow, learn and begin to compete. It’s safe to say the teacher learned as much as his students.
Life in Duxbury has changed now that COVID is in the rearview mirror.
“Now our summers are great. We spend a ton of time at the beach and on the water (in the bay), which I would have never thought could be possible. We are able to drive down to Plymouth Harbor from Duxbury in 20 to 30 minutes, eat dinner and drive back—on the water, if we want.
“It really is a wonderful place to be in the summer. The weather is never super hot and when it is, we just jump into the bay and cool down. I am very fortunate to have the job, but it also affords my kiddos opportunities like sailing, swimming and tennis at the club that even today I couldn’t afford or would be connected to if I didn’t have the position at DYC that I have.”