The Luxury Guide to Aspen Ski Vacations: Restaurants, Slopes and Afternoons

A ski vacation in Aspen can be an unprecedented indulgence — if you know where to eat, stay, and ski, writes Steve Madgwick.

This guide to Aspen will take you to the best restaurants and bars and find the best ski runs at all four resorts. From Aspen Snowmass and Buttermilk to Aspen Highlands and Aspen Mountain.

Even before the flight from Los Angeles International to Aspen/Pitkin County Airport takes off, it’s clear you’re heading somewhere special. “The flight from LAX should take an hour and thirty-five minutes, as planned, unless we get private jet traffic in the Aspen area,” says the pilot.

Aspen’s folkloric ecosystem of indulgence further materializes as the Bombardier CRJ700 cuts through the cloud cover of Roaring Fork Valley and chirps down the snow-lined runway. A host of black-windowed Escalades and Suburbans stand ready to indulge the chosen few (you) in low-key upscale stays or $15 million mansions, which often sit empty in the low season.

With four ski areas and a town-like ski resort, Aspen can be a nebulous enigma for beginners. Here, then, is where to find ski gold and pockets of high-end indulgence in this American alpine mecca, mountain by mountain.

Mecca for Ski Resort Shopping: Where Are Aspen’s Best High-End Shops and Galleries?

Walk down Aspen’s main street and adjacent avenues to browse the best shops. Downtown offers plenty of shopping to update your ski ensemble with the latest and greatest.

The Chanel boutique on East Hyman Avenue offers basic Chanel branded skis in black and white for US$9,000. And a pizza-sized matte black sled for US$10,500. Prada skis are a bargain at US$4,000. Add a matching ASPENX Prada Extreme Graphic Parka – a collaboration between the brand, ‘The Ski Pros of Aspen’ and artist Paula Crown for a whopping $5,400.

Hyman Pedestrian Mall

For Colorado ranch-style afterwear, head to Kemo Sabe. “Proudly helping football mums lead double lives since 1990,” the tagline reads. Her cowboy/girl hats and boots range from subtle to yee-haw, topping out at US$3,600 for the caiman skin zippers. Bespoke accessories worth considering include black buffalo leather purses and an antique ornamental cave bear-handled knife: US$20,000 by Jake 2 Jake.

Just following your nose on either side of Main Street is rewarded with endless eccentricities. It’s recommended to browse downtown consignment stores, such as Susie’s on East Main Street, for that pre-loved Balenciaga bargain, and shop around the galleries. The Maximillian Gallery and the Baldwin Gallery are remarkable. While the Aspen Art Museum is renowned for its New York-quality exhibits, architecture, and rooftop Saturday afternoon cafe.

Aspen Art Museum

Aspen Highlands Highlights: Cloud Nine Alpine Bistro and Highland Bowl Hike

Aspen Highlands is full of cruising blues and double black runs gliding through glades, without a green to be seen. The ski area is also home to two of Aspen’s signature experiences, each extreme in its own way.

‘Hiking [Highland] Bowl’ is peak skiing nirvana on the ‘local mountain’. From the top of the Loge Peak lift, simply climb to the highest point of the resort at 3,777 meters (45 minutes with ski/board on your back), then choose an appropriate double black line (expert only).

It is customary to evoke this achievement at every social occasion. Especially if you have booked an afternoon at Cloud Nine Alpine Bistro. The daily party in this bacchanalian bistro, where you might bump into the likes of Kendall Jenner and Will Ferrell, is judged by the number of $175 Veuve Clicquot “champagne showers”. Note: The only way to get off Cloud 9 is by skiing or snowboarding, there is no elevator access.

Cloud Nine Alpine Bistro

Is First Tracks on Aspen Mountain the best ski experience in Colorado?

“First Tracks” at Aspen Mountain is Aspen’s most invigorating ski-in ski-out experience. Before the relative masses go wild over the first “official” lifts, cut out the blank corduroy canvas (complete with guide) beneath the Silver Queen Gondola. This gondola is a virtual sky-limo compared to Lift 1, the chairlift that started it all 75 years ago.

With an insider

Aspen Mountain local knowledge helps you locate some of the many makeshift shrines hidden deep in the trees. The shrines honor the dogs of Aspen, John Denver and Major League Baseball teams.

Join the free two-hour Mountain Ambassador tour at 11:00am or opt for a private lesson for 889 USD/day to get your bearings. You’ll also hear unrivaled celebrity gossip (FYI: Elton John was adorable but a “one-run-then-done” skier).

Arguably the base of the Aspen Mountain Silver Queen Gondola (where it “lands” in town) is the best place for the afternoon. Try truffle fries and a Colorado beer on the patio at Ajax Tavern. Or a flight of caviar and a bottle of Dom Pérignon at Little Nell Wine Bar for US$1,100. Or ‘buy’ Little Nell’s private speakeasy, The Board Room, tucked away behind a pull-out bookcase and featuring a pool table, dining table and plush furnishings.

In a city with surprisingly few five-star hotels (due to the number of private residences), the Little Nell best reflects Aspen’s style and purpose. With rooms and shared spaces adorned with bold geometric symmetry and old-world textures, it’s cozy without being stuffy and well-appointed without being busy. The ski concierge, the heated outdoor swimming pool and the 24-hour room service should not make you miss anything.

Ski-in, ski-out from The Little Nell

Snowmass: large terrain, chill village, super chic restaurants in the mountains

Aspen Snowmass is a less intimidating version of the Aspen ‘stage’. It is accessible by free shuttle, 13 kilometers west of the city. Its three-peak ski area is the most diverse of the quartet, best exemplified by the blue and black snow groomers that spring from the Big Burn lift.

Snowmass also features two of Colorado’s most debonair on-snow restaurants. Swap your adamant ski boots for slippers to step into the Alpin Room for a long lunch of “reinvented Alsatian home cooking.” The meal is highlighted by the calorie-rich tartiflette – a dense fondue of caramelized potatoes and onions – and a supreme wine list with California and French dominance.

At the top of the Village Express gondola, Sam’s has a great atmosphere and even larger portions of Italian delights rich in tomatoes and burrata. Grandma’s style pizza and cannoli “flavor of the moment” will liven up your afternoon.

The Sky Cab connects the Snowmass Snow Village Mall to the Base Village. It is home to the Viceroy Hotel, a fine choice of accommodation and the location of a former Ute-inspired wellness spa. As well as the sophisticated yet lively Toro Kitchen & Lounge, with theatrical cocktails like the Smokey Colorado Old Fashioned.

Viewline Resort is in the center of the Village Mall action; the new 254-room resort features an expansive lobby bar that features live jazz and valley views, the fast-maturing Stark’s Alpine Grill, and truly ski-in/ski-out Mountain Front Suites.

Why Buttermilk Mountain isn’t just for beginner skiers and snowboarders

Buttermilk is cataloged as a family green dream of forgiving nursery slopes, which is true in a Colorado context. But it’s also home to an X Games terrain park, complete with a killer halfpipe (just ask 2019 champion Scotty James). And a lesser-known network of bustling, uncrowded blues and blacks accessible from Tiehack Express.

Take the afternoon to immerse yourself in the culinary scene of the city of Aspen. Start with a decadent lunch, favorite French Alpine Bistro, with dishes as rich as its clientele and furnishings as eccentric. Raclette, gnocchi-flettes with truffles and sweet pancakes serve as decadent fuel.

Hotel Jerome is a stylish stay choice, and its Living Room bar is a quintessentially cozy spot for a hot cocktail. I recommend you try the spicy Little Theodore. From the working days of the chaotic mining town to the Hunter S. Thompson of the 80s, Jerome has always held up a mirror to Aspen’s fortunes.

Trying the “new place” is always a must. The newest wave of Cresting Aspen is Chica. An upscale Latin American restaurant that pays great attention to its fun and fusion dishes. Meals range from lobster mac and cheese to the incredible “Flaming Skull”, a golden sugar skull that “melts” to reveal a lava cake.

For a last peek behind Aspen’s lavish curtain, dive into the Caribou Club. It’s an eccentric private cave with Warhols on the walls, stacked antler chandeliers and a wine cellar where price is not in dispute. Usually you have to know “someone”. But if you are determined, temporary memberships are available. These memberships cost up to US$2,000 per week for two people.

This article originally appeared in Volume 41 of Exclusive luxury travel and style magazine. Subscribe to the latest issue today.

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