It’s no secret that Jackson, Wyo., and its surrounding valley (known as Jackson Hole), easily boasts some of the best skiing in North America. There’s Jackson Hole Mountain Resort and its longest continuous vertical rise in the United States. And Snow King, the state’s oldest ski area and home to the steepest north-facing FIS course in the continental U.S. But it’s Jackson’s quirky charms, unassuming allure and staunch dedication to land preservation that set this former fur trappers’ outpost apart from tonier ski towns like Aspen and Tahoe.
Even with the robust tourism industry, locals take pride in how well Jackson Hole has succeeded in resisting the temptation to overdevelop its sweeping landscape. In fact, only 3% of the land is privately owned, while the rest is either state-managed or federal property, including nearby Grand Teton National Park and the majestic grandeur of Bridger-Teton National Forest.
Come wintertime, tourism certainly soars in tandem with the ski lifts, but with all the access to nature and various outdoor activities—endless hiking trails, mountain biking, horseback riding and glorious stargazing are just a few—the warmer months are actually when the area sees the most visitors. (Though, unless you’re one of the just over 10,000 town residents, you likely won’t feel too crowded-in given the geographical sprawl.) In recent years, several new hotel openings and their attractive lineups of year-round activities have solidified Jackson’s reputation as a perennial destination.
Tucked in the base of Jackson Hole Mountain Resort, Teton Village is a cozy cluster of hotels, sports shops, restaurants and favorite local haunts like the Mangy Moose Steakhouse. It’s also home to Caldera House (two-bedrooms from $2,000 for winter month), an extraordinarily exclusive luxury resort—comprising only eight suites—that opened last year after an extensive six-year construction. For one of the owners, Wes Edens, an active outdoorsman and co-founder of Fortress Investment Group (he’s also a co-owner of the Milwaukee Bucks), the $100 million project stemmed from his personal love of the area and his pursuit of the ideal mountainside retreat for his friends and loved ones.
Caldera House’s expansive, uniquely decorated suites, each with two or four bedrooms, feel more like individual chalets with their Alpine-chic living rooms, fully loaded kitchens (which can be stocked prior to your arrival), sprawling dining areas and private outdoor spaces. That autonomous sensibility extends to the hotel’s ethos that you can make whatever you want of your time as a guest there, whether it’s an epic day on the slopes, paragliding through the Tetons, or a morning of yoga and guided meditation during one of the hotel’s regular wellness retreats. Since its opening, the hotel’s curated experiences have become a signature offering. For bespoke packages for individuals or groups, the staff will build out single- or multiday activities that appeal to daredevils and Zen-seeking types alike. That they’re fantastically one-of-a-kind—a ski lesson with Olympic medalist Bode Miller, for example—makes these unforgettable moments the epitome of experiential luxury. At the risk of quoting an old credit card ad, one might say they’re priceless.
The four-bedroom suite’s expansive master bedroom designed with neutral finishings and mountain-mod decor.
Unsurprisingly, Teton Village’s hotel rates hit their highest during winter ski season. At Caldera House, they may climb as high as $20,000 per night, depending on the suite, especially around the holidays. But for nonskiers, summer and fall in Jackson Hole yield an excess of warm-weather options: fishing, golf and white-water rafting, all of which the hotel will arrange.
Guests may also rent e-bikes from Caldera House’s on-site sports shop run by Gov Carrigan, a beloved local legend known for his equipment savvy, as a more active alternative to the 12-mile drive into Jackson center. During the day, the town square pulses with pedestrians and shoppers, while long-standing institutions like the Million Dollar Cowboy Bar, famous for its stools fashioned from saddles, are perennial nighttime destinations. So are newer establishments, such as the popular Italian trattoria Glorietta at the nearby Anvil Hotel. The hotel, which reopened two years ago following a redesign under new ownership, tends to attract a younger, more urban crowd, while Glorietta’s tables are filled nightly with a mix of locals and tourists tucking into indulgent plates of handmade fettuccine and pesto campanelle, and the impressive selection of grilled meats. The delicious seasonal aperitivo cocktails alone are worth a visit.
Mornings in Jackson call for two things: coffee and carbs to fuel up for the active day ahead. Persephone Bakery beckons the breakfast and lunch crowd with its fresh pastries, mixed salads and hearty sandwiches on a rotating selection of daily breads. It’s become such an in-demand spot that a second cafe recently opened in The Aspens, a neighborhood in Wilson, Wyo., around a 10-minute drive from Caldera House. But for further proof of Jackson’s thriving food scene, there’s no need to trek to town. The biannual Jackson Hole Food & Wine festival’s third iteration will take place in March 2020 in Teton Village, only steps from Caldera House.