Travel + Leisure: The Stylish Western Ski Town Even Non-skiers Will Love

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Jackson Hole has always been a little rough-and-tumble, the kind of place that’s more about fresh powder than see-and-be-seen après-ski glitz. But even as it has held tight to that independent, cowboy-country spirit, the area has quietly become one of America’s most stylish wintertime retreats.

You’ll definitely want to wait until at least 10 a.m.,” said the tattooed pro-shop clerk, with the kind of yeah-braah stoner’s talk-laugh that makes you feel your middle age. This followed the lengthy note about “Conditions…” that arrived in a 6:45 a.m. text from our guide, Paul Boillot.

It was March, and the tail end of 2019’s record-setting, 505-inch season of snowfall in Jackson Hole, the wide valley that encompasses both the town of Jackson and the namesake Jackson Hole Mountain Resort in Teton Village. Until our arrival, the mountain had seen several consecutive bluebird days. My family and I were hell-bent on leveraging our East Coast–calibrated body clocks for full days of skiing, despite warnings of poor visibility and icy terrain. By 7:30 a.m., we were all-but-helmet ready. How bad could it be? I thought.

Paul compromised with us on a 9:30 start. We met at the Sweetwater Gondola, just steps from our hotel, Caldera House, in the heart of Teton Village. When this boutique property opened in 2018, it replaced a beloved honky-tonk — a loss that half the town was still smarting over. (Most evenings the other half seemed to spill out of the stylish yet cozy joint on Caldera’s ground floor.)

“We skied Deer Valley most recently,” I heard my 15-year-old son, Henry, say to Paul, who smiled and nodded politely. I’d later learn from the barman at our hotel that such an admission was, for Jackson Hole residents, tantamount to getting pushed into a wave and calling it surfing. We stuck to the lower part of the mountain that morning, but fog as thick as meringue all but erased any trace of the skier ahead in our five-person slalom train. We all agreed that these slopes felt different — or, as my younger son, 13-year-old Will, said, “I feel like I have banana peels on my skis.”

“The snow still needs to soften,” said Paul, sensing a dip in our confidence. “Jackson is not like any other mountain — it’s not for those who want their egos coddled.” Seeing our need for a pick-me-up, he led us down a minor chute just off the Marmot double chairlift. Without hesitation, the boys shot straight down, caught some air, and landed easily on the wide gentle run below. I, on the other hand, chickened out at the sight of the narrow drop-in — just a two-foot plunge, but flanked by rocks. “What makes it so special is that it’s a different mountain every day,” Paul said later. “You have to read the terrain, be on your toes, never get complacent.”

And therein lies the paradox of the place: underpinning the thrill-seeking badassery of those who live and play in Jackson Hole is a near-religious reverence for the elements. Long considered the ultimate skier’s mountain, it delivers a one-two punch of tough love and, just when you need it most, adrenaline-rush euphoria.

Which, once you get a taste of, I was warned, you can never quite shake. As I heard for the third time that morning about the infamous, bucket-list, double-black-diamond Corbet’s Couloir — a 10- to 20-foot drop-in — the only thing I couldn’t shake was my bruised ego.

“This place could have gone the way of Aspen or Vail,” said Erik Warner, a cofounder and principal of Eagle Point Hotel Partners, which owns the haute-hipster Anvil Hotel in downtown Jackson. Except that with the mountain’s 4,139-foot vertical drop culminating with the summit of Rendezvous Mountain at 10,450 feet, there is, as Warner said, “a high barrier to entry in this town.” And while Jackson Hole Mountain Resort prides itself on its 133 trails comprising some 2,500 acres of inbound terrain, half of which are expert slopes, it has also been investing heavily in making itself more accessible to beginner and intermediate skiers. It’s added nearly a dozen new intermediate trails, and with the unveiling this past season of the 12,000-square-foot Solitude Station — the new and upgraded ski-school center — the resort is poised to go toe-to-toe with more family-friendly winter destinations like Snowmass, in Colorado, and Park City and Deer Valley, Utah.

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