Even if you’ve never set foot in Wyoming, chances are you’ve seen the neon-lit sign for the Million Dollar Cowboy Bar somewhere on your social feed, glowing in the heart of downtown Jackson Hole. Directly across the street, the signature antler arches guard the quaint town square. And while people can already sense its magic from afar, the moment you land in the middle of Grand Teton National Park is the real giveaway you’re in for something unique.
During warmer months, hikers, kayakers, and wildlife enthusiasts flock here to take full advantage of the close proximity to Grand Teton National Park and Yellowstone’s South Entrance, just 90 minutes away. Come winter, Jackson Hole transforms into a scene straight out of a Hallmark movie—blanketed in snow and aglow with festive lights. Yet, it never feels overcrowded or ostentatious, even at the height of ski season when skiers—especially those in search of some of the most advanced terrain in the country—flock to Rendezvous Mountain for a day on the slopes, followed by après-ski fun in Teton Village.
But you don't have to be a thrill seeker, skier, or snowboarder to appreciate Jackson Hole’s awe-inspiring landscape, impressive culinary scene, and cool Cowboy charisma. Whether you’re in it for the powder or the vibes, here’s how to make the most of this winter wonderland.
There’s no single “best” place to stay in Jackson Hole—it all depends on your budget, preferences, and the experience you're looking for. Teton Village caters to skiers seeking prime ski-in/ski-out access, though that convenience comes at a premium, especially during peak season. Amangani, at the foothills of Grand Teton National Park, is a favorite among the celeb set, and there's always Airbnb for larger groups, but those looking to be in the middle of the action often opt for a spot right in town—where you can easily stroll to shops and restaurants.
Until recently, though, downtown Jackson Hole didn't really offer luxury accommodations (and none on the square). Now, offerings like The Cloudveil have changed that for discerning travelers who don't want to dip into their 401k for a vacation but still want a luxury experience. Their 100 upscale guest rooms and suites are decorated in a polished, rustic-ranch style—think wooden beams, well-worn leathers, and artwork from Jackson Hole artists. Its structure, a blend of stone, wood, and metal, nods to the historic buildings that border the square, and a spacious living room is a natural gathering place for guests around the large wood-burning fireplace, accompanied by daily live music from local musicians. Outside, a pool and Jacuzzi offer a welcome reprieve after a day on the slopes—just 20 minutes away—complete with a guest-only shuttle that makes multiple pickups and drop-offs at the base of Teton Village.
If you've come here for the award-winning skiing, you've got an Ikon Pass, or you can grab single-day lift tickets to Jackson Hole Mountain Resort, where the slopes have some beginner terrain but are a universal mecca for powder hounds. If you’d rather not haul your gear around, enlist Black Tie as your on-demand concierge so you don't have to lug around your skis (arguably, the worst part of the mountain experience). They also offer personalized fittings from hotels like The Cloudveil for rental boots, skis, helmets, and goggles if you don't have your own.
For a break from the slopes, consider an adorable Iditarod dog sled ride or head to the National Elk Refuge, just north of Jackson, to watch herds roam in their natural winter habitat. And of course, you're probably interested in some shopping. In downtown, Pendleton offers iconic blankets and outerwear, while Womenfolk specializes in vintage designer gems—think retro Fair Isle sweaters, suede and leather fringe coats, and cowboy boots. Swing by Valley Bookstore to pick up a good read, and of course, no trip to Jackson Hole is complete without capping off your day at the Cowboy Bar, a local legend and watering hole with live music and saddle-topped bar stools that create the perfect place to play some pool or practice your Do-si-do.
For a memorable mid-mountain experience, head to Piste Mountain Bistro for lunch. Afterward, ride a gondola to Corbet’s Cabin for their famous waffles. If you’re a confident skier, you can tackle the slopes on your way back down; otherwise, enjoy the scenic gondola ride back to civilization.
After a day on the slopes, kick off your après-ski at The Handle Bar inside the Four Seasons Hotel, where a spicy margarita is the perfect way to toast a great powder day. Head to the Alpenhof Lodge for drinks and lively polka for a more eclectic vibe. If you’re calling it quits before the last lift closes, the Mangy Moose is an iconic go-to, though it fills up fast—so get there early if you want a seat.
The mountain town may be laid-back, but the culinary scene—one with the world ordering its celebrated Snake River Farms beef—is anything but sleepy and rivals big-city dining with big points for creativity and flavor. Start at Glorietta Trattoria for inventive Italian fare like house-made pastas and a shareable American Wagyu Zabuton, which is something to write home about. At Bin 22, tucked behind a wine shop, you’ll find Spanish-inspired tapas—octopus, patatas bravas, and more Basque region-inspired cuisine—plus the option to grab any bottle off the shelf with zero corkage fee. If you’re craving something family-friendly, head to Hand Fire Pizza, housed in a converted theater known for its wood-fired pies. For a taste of French bistro charm, book a table at The Bistro, the latest concept from Jackson Hole Fine Dining, where bar steak, meatloaf, herb-roasted chicken, and a fresh oyster bar pair beautifully with wines from around the globe—all in a setting that feels sophisticated but, in true Jackson Hole fashion, never stuffy.
