Paying It Forward

MATT WHITCOMB LOOKS BACK AT HIS SMALLTOWN UPBRINGING AS HE 

PREPARES FOR THE WINTER OLYMPICS 

By Taylor Staubach

Photos Courtesy of Matt Whitcomb

As head coach for the U.S. Olympic Cross Country Ski Team, Matt Whitcomb’s life is often a whirlwind of international travel. “I’m all over the place,” he says, pointing at the duffel bag behind him. “Starting in the middle of November until the end of March, I’m pretty much traveling, and most of the races are in Europe.” Although his professional home is wherever his team is, it’s the Berkshire hilltown of Worthington that he credits with shaping his path and the community of people who never told him he couldn’t. 

U.S. Cross Country Ski Team head coach Matt Whitcomb and partner Caitlin Cash in Norway last winter. Opposite, Whitcomb and U.S. Ski Team coach Kristin Bourne give on-course time splits to athletes at the 2024 Minnesota World Cup. The 30K home crowd fans made it too loud to yell the info. Dry erase boards were used. 

Whitcomb will guide the U.S. Cross Country Ski Team into the 2026 Milano Cortina Winter Olympics in Italy. The event, which runs from February 6 to 22, will feature several returning medalists, including Jessie Diggins and Julia Kern. For Whitcomb, the months leading up to the games are a crucial period of training and team cohesion. He should know—it’s his fifth time coaching the cross country ski team at the Winter Olympics. 

That’s a long way from Whitcomb’s introduction to the world of competitive skiing. “I think my parents said, ‘Hey, there is this race this weekend, do you guys want to do it?’” He recalls. “We had no idea you could race on cross-country skis. And because it’s such a small place and we skied everyday, we all did pretty well.” 

That small place was Hickory Hill, a family farm in Worthington. Once known regionally for its cross-country ski trails, Hickory Hill operated for more than 20 years as a ski lodge and touring company. For decades, the farm hosted the Bill Koch Youth Ski League, and its lodge was often filled with families warming up after a day on the trails. As winters grew shorter and reliable snow became harder to count on, maintaining the trails became unsustainable for the family farm. Hickory Hill closed its ski operations in the early 2000s and is now home to Sena Farm Brewery. 

“Today, Notchview is the place to cross-country ski in Massachusetts,” Whitcomb says. Notchview, located in Windsor, is the single largest property stewarded by The Trustees of Reservations and has 25 miles of groomed ski trails. “It’s fabulous; the trails have character and offer something for all levels, and the ski club is something you should join. If nothing else, you have to see my mom’s hand-crafted troll houses that are mounted on stumps on a trail near the lodge.” 

Growing in Worthington, Whitcomb attended Gateway Regional High School in Huntington and finished at Wahconah Regional High School in Dalton, where his father taught auto shop for 20 years. “He coached the cross country ski team for three years,” says Whitcomb. “Growing up, he coached me and my brother, and still to this day a few of my friends call him ‘Coach.’ 

“It was the combo of my dad and mom that made the difference in my childhood. They got us outside, and then they helped us find our tribe.” 

What began as a handful of families meeting for weekend races quickly took off to be much more. “It became the thing to do in the area,” says Whitcomb. “Suddenly, there were about 20 to 30 families. We just sort of accidentally became really motivated." 

His love for skiing took root because he was part of a youth ski league that was started by Ed and Mary Hamel. “My love for skiing turned into a love for my friends, and my belonging to my group of friends became my confidence, purpose, and motivation,” he says. “That all happened because of Ed and Mary. Ed would become my youth coach until I went to college. The two of them hit a home run for me and my friends and for my whole family. I’ve been incredibly fortunate. Every coach I’ve had along the way—as a kid, high schooler, or as a college athlete—they got it. I’ve had it good.” 

The tight-knit group of ski families proved that a large city wasn’t needed to build energy and momentum. “It turns out you don’t have to come from a big place to compete,” Whitcomb says. “You can have folks from some little place like the Berkshires and make an impact.” 

Whitcomb led the 1995-96 Wahconah Cross Country Ski Team to a state championship and was also the Individual Mass State Champion that same season. After high school, he attended Stratton Mountain School (1996-1997) and Middlebury College (1997-2001), where he captained the ski team in his senior year. 

After graduating, he launched his coaching career with the Glacier Nordic Ski Team in Whitefish, Montana, followed by four years at Burke Mountain Academy in Vermont (2002-2006)—three of them as New England’s head coach for Junior Nationals. 

In 2006, Whitcomb joined the U.S. Ski Team as the head development coach, spending much of his career guiding the women’s team until 2018. He then served as the U.S. Ski Team World Cup coach until 2020 and is now in his sixth year as head coach of the U.S. Cross Country Ski Team. He has guided the team through four Olympic games and was named the U.S. Ski Team International Coach of the Year in 2008, 2012, 2015, 2017, and 2018. He also sits on the board of the National Nordic Foundation and lives in Burke, Vermont, when he’s not living out of his duffel bag. 

Whitcomb draws a direct line from his success back to the support he received growing up, like the time his parents let him skip school to watch the MIAA Nordic Ski Championship races. He never forgot watching the Weaver brothers dominate. (Paul Weaver is a Lenox native and two-time Olympian.) “I’d never seen anybody ski so fast,” he says. “My parents had no real motivations to turn me into a great skier. They just wanted to give me a great experience.” 

That sense of community continues to shape his coaching philosophy. Leading a team that often spends months abroad, he works to recreate the same sense of belonging and family atmosphere. “The one thing that our team does depend on is our ability to connect as a cohesive team,” he says. “We stay in Europe and can’t just go home, so the ability to function like a family is really essential for the team.” 

Matt sees that same small-town spirit reflected in the revitalization of Burke Mountain, where he coached for four years. “They are these little pockets, looking out for each other in these small remote areas that celebrate those who are doing cool things from these small towns,” he says. “Jon Schaefer will have a big impact on the Burke community. He’s a hard worker, a smart guy, and a community builder. Jon won’t settle for good. Selfishly, a few of us have asked the new owners to invest in the development of cross-country skiing in the town, and they show interest. You can only blow your knees out so many times until cross country becomes your only way of skiing!” 

For Whitcomb, it all cycles back to paying it forward. “I look back at all these things, these things that don’t cost anything, that somebody in a position of leadership supported,” he reflects. “There are people out there making a difference and they don’t even know it. That’s what the Berkshires are like.” 

The 2025-26 Stifel U.S. Cross Country team is led by three-time Olympic medalist and seven-time World Championship medalist Jessie Diggins, two-time World Championship medalist Julia Kern, and Olympians Rosie Brennan, Gus Schumacher, Ben Ogden, JC Schoonmaker, and Sophia Laukli on the “A” team. They’ll compete in the Milano Cortina Winter Olympic Games held in Val di Femme from February 6–22, and the Stifel Lake Placid Finals in Lake Placid, New York from March 20-22. 

When asked what he’s most excited about as the Winter Olympics approaches, Whitcomb says, “Watching athletes on your team win Olympic and World Championship medals turns out to be a fun thing, but what I look forward to is the lead-up. This is when we lock in together as a team and try to do something big together. For me, trying to win is more fun than actually winning.”