Tucked away in the heart of the Tetons, Jackson Hole, Wyoming, is a town where rugged wilderness meets understated luxury. Picture a scene straight out of a vintage Western, complete with a town square ringed by iconic antler arches, and you're halfway there. But don’t be fooled by the laid-back vibe; this is no ordinary mountain town. Jackson’s charm lies in its unpretentious allure, a rarefied yet approachable sanctuary that draws visitors in—many of whom never leave. And therein lies the rub. The influx of remote workers, fueled by the pandemic, has turned this once idyllic retreat into a flashpoint for debates about affordable housing, as rents soar and the local community grapples with change.
Despite these growing pains, Jackson continues to make waves for its small but mighty dining scene. Restaurants here have earned a reputation for punching well above their weight, although the pandemic and the occasional mask mandate have certainly left their mark. In winter, Jackson Hole transforms into a mecca for world-class skiing, though climate change casts a long shadow over its once-reliable snow seasons—an unsettling omen for a town so deeply intertwined with its outdoor economy. With the absence of early snow in December, the vulnerability of Jackson’s future as a ski haven becomes ever more apparent.
It’s not just the snow that’s shifting. Teton County, where Jackson sits, now holds the distinction of being the wealthiest county in the U.S., making it a magnet for the ultra-wealthy in search of pandemic-proof havens. The mythos of the rural West—the dusty cowboy, the bohemian ski bum—persists, offering a stark contrast to urban life’s moral quandaries. Jackson feels like a world apart, a place where the wilderness is pristine, the air crisp, and the ties to nature profound. The proximity of Grand Teton National Park lends the town an almost cinematic grandeur, while its architecture—an eclectic mix of frontier nostalgia and modernist flourishes—tells a tale of transformation.
Take a walk through town and the Old West still lingers in its bones, though newer steel-wrapped, glass-heavy structures speak to Jackson’s growing Malibu-meets-Mountain retreat identity. It’s no wonder some locals have christened it ‘Neverland.’ While the town’s rustic dude-ranch charm has long appealed to blue-blooded elites seeking respite, its modern architectural aesthetic seems tailor-made for the Montecito crowd.
Visiting in the off-season, from early November to mid-December, reveals a quieter Jackson, perfect for those who prefer to take it slow. For those in search of chic lodging, the Anvil Hotel—a renovated mid-century motel designed by Brooklyn-based Studio Tack—offers a stylish base with frontier-chic interiors. Think custom cast-iron beds, Woolrich blankets, brass fixtures, parquet floors, and kilim rugs that set the tone for a stay as cozy as it is cool. Nearby, The Virginian Lodge offers a groovy take on Western kitsch, with wood-paneled walls, cowboy oil paintings, and just the right amount of taxidermy for that authentic ‘old-school Jackson’ feel. As for dining? Don’t miss the elk bolognese at Glorietta, where you’ll discover a taste of Wyoming that’s anything but expected.