MATT WHITCOMB LOOKS BACK AT HIS SMALLTOWN UPBRINGING AS HE PREPARES FOR THE WINTER OLYMPICS
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Paying It Forward
MATT WHITCOMB LOOKS BACK AT HIS SMALLTOWN UPBRINGING AS HE PREPARES FOR THE WINTER OLYMPICS
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.
›› 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.
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
94 // BERKSHIRE MAGAZINE Holiday 2025