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Andrew Sheppe '00: Historic Tales and Technical Trails

Greg Kwasnik
A big part of what makes Holderness School so special are the teachers. This year, we’re taking the time to get to know just a few of the amazing educators who call Holderness home.
When Andrew Sheppe ’00 sat in Tom Eccleston’s history class at Holderness in the late 1990s, he discovered the power of history to increase his understanding of the world. It was a discovery that had lasting implications: Andrew went on to graduate from Georgetown University and work as a language analyst at the National Security Agency before eventually becoming a history teacher himself.
Today, Andrew is back where his intellectual journey started, teaching history to a new generation of Holderness students. “It’s fun to teach high school in general because you’re around when kids first discover some of the more important ideas in life,” Andrew says. “It’s fun to see them make connections and have their world expand as rapidly as it does.”
We recently sat down with Andrew to talk about his life as a history teacher, how Holderness has changed in the 20 years since he graduated, and his passion for mountain biking on campus. Here’s what he had to say.
What sort of classes do you teach?
I teach history. I teach a lot of a course called Advanced History of the West, which is a combined AP US History and AP European History course. I teach some Middle Eastern history, and I teach some electives in intellectual history about the Enlightenment. Over the past 10 years, I’ve also taught some African history.
What got you interested in History?
My own high school experience, partly. I had a really good ninth-grade high school teacher, and I liked that idea of piecing together the parts of the world and increasing my understanding but also increasing the number of questions I could ask. I remember that distinctly happening in ninth grade with a good ninth-grade history teacher – Tom Eccleston, actually – Rick Eccleston’s ‘92 father. I think ever since then I suspected I would do this, so I studied history in college, I read a lot of history in my free time. It's been, not a lifelong passion, but at least the last 25 years now.
You grew up on the Holderness School campus, correct? How has the school changed since you graduated?
I did. I was a faculty brat here. My stepfather taught here for 17 years, from the early eighties until the late nineties… One of the defining characteristics for Holderness students is the busy pace of the place, and I think that would be recognizable to anyone from the nineties – or if we took a kid from now back to the nineties. It’s a busy place where you run from one thing to the next and you don’t quite finish football practice before you’ve got to get to sit down dinner, and you don’t quite finish your homework before you have to go to bed. So that slightly hectic, but, to me, very fulfilling, fast pace is similar. There would be massive differences in things like cell phones and the internet – we got our first email accounts, I think, in 1996. But a lot of things I think would be the same – the culture, the social dynamics. Some of the adults are the same. I currently work with plenty of people I once thought were old and now seem sort of ageless to me.
You’ve spent a good deal of your life at Holderness. In your opinion, what makes a Holderness education special?
Lots of things make Holderness special. I also think some of the best things about Holderness aren’t special. I think our location can’t be beat if this is where you want to live – to be this accessible to civilization but also really in the White Mountains is wonderfully special. I think we are a 300-person community where we can get to know everybody, and a lot of high school experiences aren’t that. But I say this a lot, so I should probably say it here, but I think some of the best things about Holderness aren’t special at all. It’s important for people to learn U.S. History and everyone knows that and teaches them U.S. History. That makes it really un-unique and yet vitally important. Some of the best things we do are not unique at all – they’re actually completely standard – they’re just really important parts of adolescence and of education. I think that we should recognize that so we don’t run away from what’s good in order to be special.
You also coach the mountain biking team. Tell me about that.
That sport – across the country and definitely in this region – has really taken off, so there are lots of riders now who didn’t used to ride and lots of trail networks that didn’t previously exist. I’ve been around to witness a real explosion in that sport. The league grows every year, it’s really fun. It’s a hobby of mine, in addition to being my job. So as soon as the spring rolls around, even though it’s not mountain bike season, I take my bike out and ride and my kids and I like to build trails on the school property. So, mountain biking is something I feel a little bit guilty about getting paid to do because it’s a lot of fun.
You build trails on school property?
We’ve got 600  acres on campus, a lot of which is our Nordic trail network behind the gym. Ten years ago, we had a few little singletrack mountain bike features, primarily downhills, that kids had cut out there to have a more interesting downhill experience. Riding on Nordic trails is a little boring because they’re so wide. We set the goal early on of connecting all of the different little fragments together into a big loop. Now we’ve got about five miles of singletrack and a couple of different loops that cross and recross our Nordic trails. You can ride for about an hour without doubling up much of it. So you’ve got an hour’s worth of pretty technical singletrack. We didn’t build it for beginners, unfortunately. The next project is to put in some green trails for our beginners, to ease them in a little bit.
The mountain biking team spends one day a week building trails on campus – or helping to maintain trails in the area. Why is that important?
We build trails because it’s fun to build trails, and because it’s part of the mountain biking ethic – if you ride, you should work on trails somewhere, because that’s how trails exist. We do that as sort of a giveback, a community service. We’ll race on Wednesdays, and that’s quite tiring, so we’ll give our legs a recovery day on Thursday and break up into teams of five or six kids and grab shovels and rakes and loppers and head out into the woods and either scout and cut and rake new trails or maintain old trails. So if you ride a given sandy berm for five years it wears out and erodes and so we have to go add dirt back to places we’ve overridden. But we add at least a little bit of trail every year. That’s how we’ve gotten to the five miles we’ve got now.

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