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Daniel Hand High School math teacher Jason Engelhardt has helped create a 15-mile network of mountain-bike trails in Madison’s Rockland Preserve. Photo by Tom Conroy/The Source

Daniel Hand High School math teacher Jason Engelhardt has helped create a 15-mile network of mountain-bike trails in Madison’s Rockland Preserve. (Photo by Tom Conroy/The Source | Buy This Photo)

Jason Engelhardt: The Hand Math Teacher Goes Off the Beaten Path

Published Sep 28, 2016 • Last Updated 01:35 pm, September 27, 2016

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Educators are often praised for being trailblazers. Jason Engelhardt, who teaches math at Daniel Hand High School, in Madison, literally deserves the compliment.

Jason is the driving force behind the creation of a network of mountain-bike trails in the town’s Rockland Preserve that has helped turn the preserve into a destination for bikers throughout the Northeast. In fact, the network, which is 15 miles long and growing, was recently chosen by the mountain-biking website as the best in Connecticut.

“We are the best,” says Jason, smiling, “but it’s nice to have someone else say it.”

Jason started working on the Rockland trails in 2012. As the adviser to Hand’s mountain-bike club, he would ride with the club members in the preserve. They asked the Rockland Preserve Advisory Committee if they could help clean up some of the damage caused by hurricanes Irene and Sandy.

“We helped them with cleanup,” Jason says, “and that kind of built trust. And then it became my own project from there to start a trail-building project at Rockland Preserve.”

Jason constantly reiterates that the trail project has been a group effort.

“It’s not a one-man show by any stretch,” he says. “In our first two years, we had over 4,000 volunteer hours of work.

“We’ve built 15 miles of single-track trails that abut to five miles that we built on a Durham property called Pisgah,” he says. “They have become the most popular bike trails in Connecticut.

“This preserve was not really used to its full potential,” he says, “and now it’s gone from maybe, like, 20 to 50 users per week when it started to well over 500 users per week.”

Jason says that slower-moving nature lovers needn’t worry about being run over by helmeted maniacs. For one thing, the single-track trails—ones that are only one user wide, whether it’s a biker or a hiker—are set deeper in the woods.

“In 650 acres,” Jason says, “there can be 25 bikes around you and you never see one because they’re so far in.”

What’s more, Jason says, “we try to make sure that there’s a standard of use and responsibility among the bikers, so that they understand how to share the trail, how to participate safely to minimize their risk and anybody else’s risk. We have a mountain-bike code that we have posted at all the trailheads and online at the town website.”

The trails, Jason stresses, are meant to be shared.

“The purpose for our design was for mountain bikes,” he says, “but it’s also very friendly for trail running, cross-country skiing, hiking, [and] snowshoeing.

“Everything, even the easy trails, requires skill and fitness,” he says, “so we are always integrating challenges, because that keeps people interested and coming back. That’s why we love it. We don’t go to have an easy day. We go to work hard. Those challenges, and how to make them, become the passion.”

Jason says that his experiences in Rockland have helped him professionally as well.

“Building mountain-bike trails has absolutely affected the way that I teach,” he says. “The process of building that trail network has been my transformative experience and has allowed me to gain competence and realize my own abilities in ways that I didn’t know before.

“Problem solving, risk acceptance, and taking on a challenge have really opened my eyes to the way that people prosper,” he says. “You don’t prosper by not taking risks. You have to try difficult things in order to get better, and I’ve noticed in teaching that it’s very easy to give students the path of least resistance, but it’s almost never in their best interest.

“When I build features in the preserve,” he says, “I build them sometimes knowing I can’t do it, it’s not in my range, but it’s possible that other people will like it, and it’s safe. As long as those constraints are held in play, that’s what’s going to bring people there. To always have something slightly out of reach is really important.

“So when I’m teaching—today we taught systems and equations with three variables, and it was a real stretch for some of the kids in the room. I look at it the same way. If I keep giving them the same thing that’s routine, they’ll never grow, but by allowing them to reach for something, they’re going to get it or fall short, and if they fall short, they’re going to feel compelled to try again, and it’s going to keep them coming back, and that’s where passion happens.

“It’s like if you’re in the middle of the woods, right? How are you going to get home? What’s next? What are you going to do? And if you’re in the middle of class, and you’ve got another trimester with me, what are you going to do?”

In the spring of 2015, Jason used his brush-clearing skills to help create a teachable moment. He led a group of students who wanted to restore the remains of Camp Hadley, a Depression-era Civilian Conservation Corps camp off Copse Road in Madison.

“We cleaned up the sites, and put in posts with signs that interpreted each one of the locations,” Jason says.

Jason came to love biking the way most of us did, as a kid.

“It’s as simple a passion for me now as it was for me then,” he says. “Just going out and playing with friends.”

Born and raised in Middletown, Jason attended the University of Mary Washington in Fredericksburg, Virginia, earning a bachelor’s degree in economics. After college, he joined AmeriCorps.

He was assigned to a job in Rochester, Minnesota, where he helped workers in nonprofits improve their use of technology.

“It was then that I realized I was having so much fun doing the teaching,” he says. A job as a high school rowing coach confirmed his decision to be a teacher.

Jason became a New York teaching fellow, working for two years at a school in Queens while earning his master’s degree in education. He met his wife, Katrina, at a summer camp in Baltimore for gifted and talented kids at which he was a counselor and she was the nurse.

After Queens, Jason worked at Madison’s Polson Middle School for four years; he has been at Hand for eight. Katrina has worked as a dental hygienist and teacher. She is currently a part-time art teacher at the Town Campus Learning Center, Madison’s inclusive preschool, and at Island Avenue Elementary School.

Jason says that since he and Katrina have started their family—they have a four-year-old daughter, Zoe, and a two-year-old son, Silas—he’s had less time to do the hands-on work on the mountain-bike trails; he’s now more of a manager. But he did manage to find time to singlehandedly clear a trail in the Neck River Uplands North, a preserve owned by the Madison Land Conservation Trust that’s near Jason’s home.

In gratitude, the trust allowed Jason to pick the name for the trail. He called it the Annyka Harper Trail, using the middle names of his children.

That rather oblique name reflects Jason’s general tendency to avoid taking too much credit for his work. He can rattle off a long list of people who have contributed to the Rockland trails, citing two people in particular: Joe Oslander, a former Hand teacher and principal who is on the Rockland Preserve Advisory Committee (“He has been my mentor at Rockland,” Jason says), and Jon Petersen (“He is the like the guru,” Jason says. “He is the most accomplished trail builder in central Connecticut, and he took interest in this project, and now some people think he lives in the woods”).

Like most of us, Jason prioritizes.

“I limit my focus on the things that matter most to me,” he says. “The trails are so important. My family is the most important, and I love what I do here at work.

“I’ve always said that the reason why I’m inspired to do this work is to create a world I want my kids to grow up in and to create a town and a place with things that I wish I had when I was young.”

But Jason thinks the trails can be transformative for adults, too.

“They can be passionate about something or love something that’s healthy and only leads to more health,” he says. “Because you get in, and you start really loving the sport, and you start to appreciate the wild spaces and preservation. That’s what happened to me, and it happens to a lot of people.”

To nominate a Person of the Week, contact Tom Conroy at

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