Meet the Retirees Who've Become the Ski Bums They Always Wanted to Be

Amber Day

This is part of a collection of stories celebrating the many shapes retirement travel can take. Read more here.

Henri Rivers, 62, has been skiing since he was 8. It all began when he snuck up to the attic of his parent’s hotel in Big Indian, New York, and found a pair of boots and skis that a guest had left behind. He took them out to the nearby Belleayre Mountain, and even though the boots were ill-fitting and the skis six feet long, he managed to hurl himself down the hill, mimicking what he saw other children doing.

“[It] was the Abbott and Costello movie, Hit the Ice,” Rivers, who now lives on Long Island, says, referring to the film's constant hijinks on skis. Despite the rocky introduction, Rivers eventually got the hang of the sport and it would become a major part of his life. By adulthood, he’d mastered skiing and begun coaching in his free time.

Rivers could never fully commit to his favorite pastime while working as a renewable energy consultant in New York City. That all changed when he retired—and the same is true for others who, during their career lives, relegated skiing to weekends and the occasional trip. Like Rivers, they discover a sense of freedom after clocking out for the last time. Finally, they have an open agenda to explore new trails, and spend weeks visiting some of the best slopes in the world. Another perk: accessing fresh powder at off-peak times, when everyone else is at work or school.

Rivers isn't the only one skiing into his golden years. The average age of skiers is increasing, which means people are staying on the slopes longer than ever. According to the National Ski Areas Association, there's a “gradual aging trend" as record numbers of skiers take to the snow (the 2023 season ended with a whopping 65.4 million people visiting US ski resorts). Resorts are catering to older visitors, too, with “Ski Free” days for those over 70, 80, or 90.

These retirees are not flying south for the winter.

Rivers is now the president of the National Brotherhood of Snowsports (NBS), an organization that encourages Black people to take up skiing and other cold-weather sports. He never misses the annual NBS summit (this year at Big Sky; last year, at Vail) which brings together chapters of snowsport enthusiasts from around the country. Skiers of all ages, even into their 80’s, come out for the days of kinship and camaraderie, he says.

But outside of NBS summits, Rivers is always chasing that fresh powder. His favorite destination is “any mountain that has snow,” he jokes, though he's regularly beelining from New York to Snowmass or Aspen. “I make sure to ski at least 50 days a season, as long as I’m injury-free.”

“There was a time in my life in my 20s where the only furniture I had was a pair of skis.”

Carolyn Stempler

When Carolyn Stempler retired from the nonprofit sector, she committed to 365 days a year of slope-side living. She was determined to ski more regularly, so she relocated to her favorite mountain—Big Sky, Montana—with her husband (the two actually met at an NBS event in 2004; she's been a member for 40 years). Stempler always knew she would retire to a ski town. "There was a time in my life in my 20s where the only furniture I had was a pair of skis,” she recalls.

Now Stempler is technically retired, but she keeps busy. She volunteers as the executive director of Women of Winter, a nonprofit that offers scholarships for women of color to learn to be ski instructors. Plus, she's a children's ski teacher herself, a prospect that always excited her.

“As a retiree, I am now able to follow my passion of instructing children," says Stempler. And it's not just about skill-sharing. “Since most [instructors] aren’t people of color, I am able to provide an opportunity for [students] to see someone who looks like me—a person who is kind, empathetic, and caring—which hopefully will make a difference in the lives of that generation,” she says.

Stempler originally asked the resort if she could volunteer, but had to take a paid job due to regulations around instructing—so, she saves her paychecks and donates them to Women of Winter. Her job perks include daily access to the slopes, where she is known as the guide with gummy bears in her pocket.

This hack is a known one among retirees: work or volunteer at ski resort, get free lift tickets. Ontario-hailing Bob Lingman, 76, also works and skis at Big Sky resort. Instead of instructing, though, he volunteers as a mountain guide. Aside from the pure enjoyment he gets from helping visitors find their way around, he's most certainly a fan of the unlimited ski access. “Prior to retirement, I had a 14 hour drive to get to Big Sky,” says Lingman. He has since retired to Bozeman, which is one hour away by car, and “skiing is more rewarding than ever,” he says.

Lingman starts his day by putting on the signature green guide jacket and arrives to Big Sky around 8 a.m. “I go into the Hungry Moose and have a bagel and coffee, chat with friends, do some meeting and greeting," Lingman says. "Then at 10, I head up the mountain for my tours.” His day ends around 3 p.m.—on off days, he is still up early tackling errands, spending time with his family, and unsurprisingly, strapped into his skies.

“When I worked at Sugarbush in Vermont, there were quite a few octogenarians who were regulars. When I grow up, I want to be one of them.”

Eric Ascalon

While he once opted for 50,000 vertical feet a day at resorts around the world, he now enjoys more relaxed skiing at Big Sky. He does have to perform a yearly skills test, which he manages just fine. He has no intentions of retiring from the slopes anytime soon.

Lingman is the kind of skier Eric Ascalon hopes to be one day. At 52, Eric Ascalon might seem too young to fit in with the retired ski bum crowd, but in his current phase of semi-retirement, he knows what he's working toward. Mid-pandemic, Escalon explored the work-to-ski lifestyle while operating a lift at Sugarbush in Vermont. “Sugarbush is a real skier's mountain,” he says, with lots of variety and a down-home feel.

Ascalon got his start skiing in college—and once he stepped back from corporate law in his 40’s, he began to ski even more, all over North America. But he's most fond of the snow he learned on, on the East Coast. “Most of my skiing has been in the Poconos and even to this day, it's where I go most.”

When he’s finally ready to stop working, he wants to build a cabin in northern Vermont or the Adirondack region. And he knows exactly how he'll spend his days. “When I worked at Sugarbush, there were quite a few octogenarians who were regulars. Some had a pronounced gait when they walked. But when they donned their skis, they sailed down the mountain with grace and pose. When I grow up, I want to be one of them.”

Originally Appeared on Condé Nast Traveler