A Weekend in Aspen
Stunning views, après-ski, bespoke cowboy hats, and a Kevin Costner encounter
For years, Aspen has been a winter wonderland for the rich and famous, but this winter, the snowy resort has gotten super hot.
Fueled by a lavish wedding rumor between Jeff Bezos and Lauren Sanchez and celebrity sightings of Mariah Carey (fresh off her “Queen of Christmas” duties). Jennifer Lopez, Kate Hudson, and Kevin Costner (who owns the Dunbar Ranch a few minutes from town); this lush ski resort is officially the “it” destination for the season.
I just returned from Aspen and, even with all these celebrity sightings, the town manages to retain its small-town Western mountain vibe. For instance, while there is a Hermès shop in town, it’s flanked by little mom-and-pop places and although you can spend hundreds of dollars on a meal, there are also indie sandwich shops, dive bars, and coffee places.
And, while you can spend a weekend in Aspen just shopping and strolling, it’s undeniably a ski town as evidenced by the exquisite view of the mountains no matter which way you turn. Take some time to stroll the John Denver Sanctuary and you’ll likely find fresh animal tracks in the snow — a gentle reminder that you’re in one of the most beautiful (and still very wild) parts of the United States yet minutes from five-star hotels and other creature comforts.
Where to Stay
If you have unlimited means, Kevin Costner’s Dunbar Ranch is available for vacation rentals. The ranch, named after Costner’s character in Dances With Wolves, consists of three residences on 160 acres of pristine lakeside wilderness with mountain views just a few minutes from town. There’s also a baseball field to play out your Field of Dreams moments. The ranch costs $36,000 per night to rent out.
Back to reality, Aspen has a host of beautiful properties that are a bargain when comparison shopping to the ranch.
I stayed at the W Aspen, a charming hotel that offers contemporary ski chalet vibes and is located around the corner from the Aspen Mountain Gondola which takes you to the top of the mountain.
I arrived just before midnight after my connecting flight was canceled and we had to drive from Denver, and I was warmly greeted with a much-welcomed glass of sparkling rose (there’s also local craft beer if you prefer). My king room was decorated in what I would call, “Don Draper goes skiing”, with a faux fireplace vent over the honor bar, cozy fur throws, and a lighted vanity area. Most welcome was a humidifier in the closet — a must when mixing altitude with apres ski time to stave off headaches, I was advised.
If you come to Aspen to enjoy winter sports, the W Aspen also has ski storage (if you’re bringing your own gear), a ski rental shop (if you decide to hit the slopes after all), and a rooftop complete with hot tub and fantastic views. The property also has a daytime dining room, 39 Degrees, that transforms into the HaSalon pop-up in the evenings, along with Hidalgo, a superior tequila bar (more on that later).
Where to Eat
Swedish Hill
If you’re looking for lunch with a view, head to the Aspen Art Museum. Take in some of the exhibits (the museum is free), then head to the rooftop for lunch at Swedish Hill. This restaurant offers salads, sides, pastries, and sandwiches paired with a direct view of Aspen Mountain.
Sundeck
Even if you don’t ski or snowboard, you simply must ride the Silver Queen Gondola to the peak of Aspen Mountain. There, at 11,212 feet, catch breathtaking views of the Elk Mountains and grab a bite at Sundeck. The casual restaurant also houses a Lavazza coffee bar in the mornings and a full-service bar. Take your Aperol Spritz to the patio to enjoy the vistas après-ski.
Ajax Tavern
At the base of Aspen Mountain, Ajax Tavern offers bistro fare with a ski lodge slant (think giant mounds of truffle fries, a grilled cheese-and-tomato soup combo, and cheese fondue to share). Sit outside under the heat lamps on a sunny day and watch the snowboarders finish their run so close that you’ll frequently get hit with the lightest waft of chill snow from their shred.
Aspen Public House
The perfect place for a quick snack or a beer, Aspen Public House gives off an authentic old-school vibe. There’s a good local craft beer selection, along with good pub grub.
Matsuhisa
Chef Nobu Matsuhisa’s Aspen restaurant offers fresh fish, an outstanding wine collection, and celebrity sightings. Jeff Bezos recently bought out the restaurant for a dinner party last week. You can do that, or just make reservations for two.
HaSalon
At first, it might seem interesting that Major Food Group decided to open chef Eyal Shani’s experiential Mediterranean concept, HaSalon as a pop-up at the W Aspen Hotel instead of, say, a sure thing like Carbone. But on opening night, the restaurant was popping with celebrities, influencers, and partiers who waved white napkins, sipped cocktails, and dined on beet carpaccio and steak and tomato ovaries (as it was noted on the menu). If you’re looking for a romantic place to canoodle by a fire, HaSalon isn’t it…but if you’re seeking a high-energy, DJ-driven night to remember with friends, this is a good choice.
Steak House No. 316
For a more traditional experience, Steak House No. 316 fits the bill. Located in a darling little house, Steak House No. 316 gives off a lively yet intimate “Wild West Bordello” vibe. Large portions, perfectly cooked meats, and well-made cocktails make this a great choice for dinner.
Where to Après-Ski
J-Bar at the Hotel Jerome
Years back, J-Bar was home to cowboys and miners. Now — it’s socialites and celebs that come to knock back a few in the modern-day ritual known as après-ski. Grab a craft beer or a sparkling rose and channel Hunter S. Thompson — a regular in his day.
Bad Harriet
Beneath the historic Aspen Times building you’ll find Bad Harriet, named after the wife of the Hotel Jerome’s original developer and proprietor, Jerome B. Wheeler. Bad Harriet feels like the place where wealthy silver miners of yore would go to celebrate a good day. Cocktails are truly innovative and presented in gorgeous vintage glassware. This is a stunning place to sip a libation or two.
Hidalgo
Employees Only’s Dushan Zarić only opened Hidalgo, an agave spirits bar at the W Aspen, a few weeks ago yet it’s the hottest place in town for people who prefer a good cocktail and great vibes over the “see and be seen” clubs. The margarita I had might well be the best one in 2024, which says a lot since I’ve had my share. Open late, Hidalgo is the place to go to meet interesting people and sip on interesting drinks. A total win-win.
Things to Do
Skiing and Snowboarding
Scratch Aspen’s fabulous surface and you’ll find a town meant for outdoor sports at its heart. That means hiking in the summer and skiing and snowboarding in the winter. The Aspen Snowmass area has multiple alpine and cross-country ski trails, including Aspen Mountain, which is so close, you’ll see people walking with their ski boots onto the Gondola.
John Denver Sanctuary
Though John Denver was born in New Mexico, he will forevermore be synonymous with Colorado. Denver fell in love with Aspen and made it his home. He wrote Annie’s Song while skiing Aspen Mountain after a tiff with his wife, and the entire town resonates with his voice. The John Denver Sanctuary, a short walk from the gentle bustle of the downtown shopping district, provides a beautiful space to commune with nature. Nestled alongside the Roaring Fork River, the sanctuary offers a garden where Denver’s lyrics are carved in stones. On a recent visit, the sanctuary was covered in fresh snow and the tracks of rabbits, squirrels, deer, elk and more could be found near the river. Truly a magical moment.
Kemo Sabe
Aspen is no stranger to high-street shopping. The affluent town is home to Hermes, Gucci, Dior, and
Golden Goose where you can design your own bespoke sneakers. But, if you’re looking for a one-of-a-kind purchase, head straight to Kemo Sabe.
Kemo Sabe is where the rich and famous come to cosplay cowboy — the store is filled with stunning silver jewelry encrusted with chunks of turquoise, boots, belts, and bags — but the main attraction are the cowboy hats, which start at about $300 and can go up to the thousands. Each hat, however, is a custom work of art. They’re individually fitted to your head before the fun starts: You can brand your hat and festoon it with bands, beads, sparkles, playing cards, feathers, and even vintage brooches.
A visit to Kemo Sabe is as crucial to a visit to Aspen as an après-ski moment. I met one of the hatmakers at Hidalgo on my first night in Aspen and he invited me to come down and check out the hats (no obligation). The next afternoon, I strolled in. As I shopped, I was offered a beer from the blue fridge in the back of the store (there’s also a bar upstairs that is rented out for private parties).
I suddenly found myself talking to Kevin Costner, who was walking through the store in a tan barn jacket and shades. I mentioned I was a huge fan of his work and the store manager added, “We all love Yellowstone.” “If you love Yellowstone, you have to go see Horizon,” said Costner, flashing that same smile he used on Susan Sarandon in Bull Durham.
At that very moment, I fell in love…with Aspen.