An Insider’s Guide to Jackson Hole

It’s 4 o’clock on a Friday in mid-December, and I’m sitting at the Four Seasons Jackson Hole’s Handle Bar trying to finish writing a story before the sun drops behind the Tetons. I've been invited here for the weekend by my old friend Kendra Kolb Butler, a beauty executive-turned-entrepreneur who made Jackson Hole the home base for her family—and her other baby, Alpyn Beauty—over 10 years ago.

It’s still technically a workday—and this bar seems like as good an office as any. But just as I am getting into a groove, the bartender leans over and says, “I need to warn you—I’m about to ring the bell.” She’s standing next to a large iron cowbell, poised to strike, as four men line up behind a makeshift wooden ski lined with shot glasses. On cue, she rings it, and the men tip the ski back, guzzling shots in unison. “Core memory unlocked!” one of them shouts, his goggle-marked face still wind-whipped from the mountain.

Into the Wild

Jackson Hole isn’t just a valley—though technically, that’s what it is: a long, glacial basin flanked by the Tetons and the Gros Ventre range in northwest Wyoming. It’s also shorthand for a strange and fascinating convergence of worlds: ranchers and real estate magnates, ski patrollers and Silicon Valley retirees, all folded into a town that still smells faintly of woodsmoke. Elk routinely cross the highway near Albertsons. At the Cowboy Bar downtown, saddles double as barstools. And yet, a few miles away, the Four Seasons serves $30 hot toddies in a lobby where the fire never goes out.

In winter, the draw is obvious: 2,500 acres of unforgiving terrain, no beginner slopes at the summit, and that dry, high-elevation powder that turns out-of-towners into lifers (Kendra, who moved here on a whim in 2015 and never left, being one of them). Come summer, the valley softens—fly fishing lodges, meadows lit up with lupine, and trailheads that seem to vanish into the sagebrush. It’s the rare place that manages to feel both remote and refined. Even the tasting sauces at Steadfire Chophouse—spruce tip béarnaise, huckleberry steak reduction—seem designed to remind you: you’re in the wild, but you're not roughing it.

No Bunny Slopes Here

After a quick stop at the ski concierge—where I was fitted with demo skis, poles, and boots—we headed straight for the slopes. A word of warning: Jackson Hole doesn’t ease you in. The Aerial Tram climbs 4,139 vertical feet to the top of Rendezvous Mountain (10,450 feet), and when the doors open, the mountain drops away in front of you. The terrain is steep, technical, and unrelenting, with long fall-line runs, tight chutes, and, on this visit, icy mogul fields that forced us to stay sharp or suffer the consequences. The runs are long with very little flat terrain to give your quads a break (and, as my friend noted more than once, many of the double blues could easily pass for black diamonds at any other mountain). Though I've been an avid skier my whole life, it was my first day on skis in three years, and by the end of the day, I was winded, wobbly—and ready for a cocktail.

Amy in Perfect Moment's Polar Flare Down Jacket and JG Bib Ski Pant. 

Après-Ski

By late afternoon, the après scene was in full swing. Outside, a DJ spun mellow house tracks near a long glass fire wall that radiated heat like a hearth, while clusters of skiers lounged with beers and cocktails, their cheeks pink from the cold. I sank into an outdoor couch with a glass of wine and watched the light fade behind the mountains.

Later, we hit the outdoor hot tub—a steaming, pine-ringed pool with a view of the slopes and just enough steam to make everything feel a little surreal. Teenagers and little kids floated beside couples sipping wine from stainless tumblers. Everyone seemed a little sun-drunk and happily wrecked from the day.

Before dinner, we wandered into the hotel’s hidden speakeasy—a velvet-draped, low-lit room tucked behind the main bar. We chatted with the bartender, who told us stories about the hotel’s early days and pointed out the booth where a few notable names had once held court.

How Locals Combat Altitude Dryness

At this altitude, your skin doesn’t just get dry—it cracks, flakes, and turns red and raw, especially after a long day of skiing. Locals know the drill: lip balm in the glovebox, hand cream in every jacket pocket, and, when things get really dire, a barrier-repairing facial. And so, before hitting the slopes on Sunday, I headed over to the Four Seasons' spa for the resort’s signature Alpyn Wildcrafted Facial.

Kendra created this clean skin-care line shortly after moving to Jackson Hole, where the air is notoriously thin. “This elevation turns your skin into parchment paper,” she explained over dirty martinis later that day in the Ascent Lounge. “When I first moved here, I couldn’t find anything that helped.” With a background in product formulation (she worked alongside dermatologist Dennis Gross for many years), she immediately set to work creating a line that used local high-altitude herbs and extracts like huckleberry, ghostberry, and wild nettle. “These plants have special compounds that allow them to thrive in extreme alpine conditions,” she told me.

I expected a little hydration and a nice massage. What I got was one of the best facials I’ve ever had: thorough, glow-inducing, and deeply relaxing. Violette, my aesthetician, started with a creamy cleanser, followed by the Pore Perfecting liquid. Then she layered on the Super Sculpt Serum and the Barrier Repair Cream, all pressed into the skin with upward strokes and cold globes that sculpted my cheekbones and depuffed my eyes. I left the treatment room with my skin dewy and radiant—and skipped foundation entirely that day.

Reset at 6,311 Feet

Ultimately, what made Jackson Hole so memorable for me wasn’t the luxurious amenities or service (though there was plenty of both at the Four Seasons), but the way the entire experience invited me to feel more. On our last night, I sat in the outdoor hot tub as snow fell softly on my shoulders and steam curled into the cold night air. My legs were sore, my lungs full of alpine air, and for the first time in months, I felt truly present. The stress I’d been carrying—family logistics, looming decisions, the low hum of anticipatory grief—seemed to lift, replaced by a rare and welcome quiet.

On the drive home, I made myself a quiet promise: Not to let another three years fly by without clicking back into my skis.

Where to Eat and Drink in Jackson Hole

Dining

Steadfire Chophouse
New-school steakhouse with old-school swagger. Great martinis, great lighting, great everything.

The Handle Bar
Michael Mina’s upscale pub inside the Four Seasons is a post-ski must for elk chili and people-watching by the fire.

Kampai
Unexpectedly chic sushi, flown in fresh and plated with the kind of restraint that makes you think you’re in Tokyo.

Osteria
Rustic Italian inside Hotel Terra. The house-made pastas and cozy mountain vibes hit hard after a day in the powder.

The Bistro
Lively brasserie inside The Cloudveil—come for the oysters, stay for the pomme frites.

Osteria; The Bistro

Bin22
Wine bar meets Spanish-style tapas spot with a killer bottle shop attached.

The Kitchen
Inventive but unfussy—this is where local chefs actually eat.

Snake River Grill
Jackson’s special-occasion standby. Think cowboy luxe, with white tablecloths and steak-tartare pizza.

The Blue Lion
A Jackson institution. Order the rack of lamb and settle in for live acoustic guitar and the occasional marriage proposal.

Persephone
The local answer to Gjusta. Come early for the kouign-amann, stay late for the best-in-class chocolate croissant.

The Kitchen (credit: Rachel Zaccardo); Bin 22 (credit: Jay Nel-McIntosh); Snake River Grill

Cocktails

Mangy Moose
Funky, scrappy, and always a scene. Après starts early and ends...whenever you want it to.

Million Dollar Cowboy Bar
Taxidermy, saddle barstools, and live country music. Yes, it’s touristy. Yes, you should go.

Mangy Moose; Million Dollar Cowboy Bar