Employee Community: A Sit-Down With One Of Stratton’s Most Admired Snowboard Instructors

Dennis Gallagher has been instructing here at Southern Vermont’s highest peak for 20 years and has no plans of stopping anytime soon. That in itself says a lot. An avid snowboarder, surfer, hockey player, devout husband, father, and all around great person to have a chat with. We sat down with Dennis and talked about his journey to Stratton, his time here as an instructor, and what plans he has for this season and the future. Enjoy!

What is your position at Stratton?

Snowboard Instructor at the Mountain Sports School.

How long have you been instructing at Stratton?

This is my 20th season, I came here in 2003. I started as an instructor — there was about two weeks of training which involved riding with other instructors, getting to know the mountain, and shadowing lessons. I started off doing big group lessons.

Prior to starting at Stratton, had you snowboarded before?

So, the first time I ever tried snowboarding was in 1994, I took a snowboard lesson at Snow King Resort in Jackson, Wyoming. I ended up skiing the rest of the week because we were in Jackson and I didn’t want to be on the beginner hill the whole trip. Between when I got back from that trip and when I moved to Stratton, I maybe went 10 times total. When I moved to Stratton in 2003, I initially thought I wanted to be on Ski Patrol but shortly after settling in, I met a group of snowboard instructors who were very welcoming and in turn, I fell in love with what I still do here 20 years later.

You’re a surfer – were you into surfing before or after getting on a snowboard?

I was into surfing and in the late 70s/early 80s, a lot of the people I was surfing with were getting onto snowboards. It was always in the back of my head, but I was going on surf trips to Rincon, PR in the winter time and remember looking at these same friends who would go to the mountains for the winter and thinking, “That’s ridiculous.”, but I laugh about it now.

What was the main reason you decided to go with instructing?

I think it was the group of instructors I met right when I moved here. I went out one of my first nights and ended up meeting a group of about 15 instructors who even after hearing that I was fairly inexperienced, convinced me that I would be fine and that I would love it. I left that night and said, “I’m gonna do that.”. Here I am 20 years later.

What is your favorite type of lesson to teach?

There’s not one, but I really like when the person comes that has never done it, they tell me they’re not a physical person, they think they will be no good at it. I like that the most because it poses the biggest challenge. It’s not that the guest is being negative, they’re just being honest. I have 3 hours to make as much progress as possible with this person, and when it works out, and the person decides it something they want to keep working at, that to me is what makes that lesson my favorite.

You mentioned the BART Center – could you explain what the BART Center is?

The BART Center’s full name is ​The Bart J Ruggiere Adaptive Sports Center and it’s a program that offers ski and snowboard lessons for people that have a cognitive and/or physical disability at Bromley, Stratton and The Hermitage Mountains. I started volunteering at the BART Center about 10 years ago at Bromley, prior to it’s expansion to Stratton. They started doing it here at Stratton a couple of years ago and after talking with the director, I decided to start helping at again this season. I am actually meeting the boy I am instructing this afternoon and I’m looking forward to it.

Fast forward 20 years, what keeps you going?

Over the years, what keeps me going are the relationships I’ve made and continue to make while instructing. Now that I have been doing this for so long, I’m finding that I am teaching the kids of people who I taught 10+ years ago. It’s an awesome feeling seeing people come back years later, the same people who were hesitant about snowboarding in the first place, having it be their favorite thing in the world and even getting their kids into it too. It’s really cool.

Do you have any advice for potential future instructors?

Get up here and meet people! I found that by going to social events around the mountain, everyone I met was extremely kind and welcoming and it resulted in me getting into instructing. As far as wanting to teach, learning from other instructors is something I do everyday I’m out there. It could be a first year instructor, and if I hear them provide a solid tip or piece of advice, I will implement it into my lesson as well. That’s the best part about it. We all instruct differently and can learn from each other every day. In summary, meet and ride with as many people as you can. Get in the middle of it – people up here love to help you succeed.


It’s always a pleasure chatting with Dennis, and we are stoked that he agreed to sit down with us and talk about his experience here at Stratton. We hope this urges people to get up here, take a lesson, or teach a lesson! Dennis’s story is a testament to the fact that it’s never too late or too early to begin instructing, or to even begin snowboarding or skiing. If you decide to take a lesson with us, be sure to request Dennis. He’ll get you turning in no time.



Published by Harley Smith on 1/27/2023