Aspen is synonymous with luxury, perhaps to its detriment. Yes, you can run into Real Housewives on the street; yes, there’s always a line outside a shop selling bespoke cowboy hats. But for those in the know, Aspen has more to offer. Its true allure for gnar-seekers lies in its rugged, high-octane terrain. The resort’s four mountains offer something for every level, but it’s on Aspen Highlands that you’ll find some treacherous lines. In fact, these two peaks offer some of the most challenging in-bounds skiing in North America, a perfect foil to the town’s polished reputation.
At Aspen Highlands, the legendary Highland Bowl is a milestone for any serious skier. This backcountry-style experience is a hike-to salmagundi of steep, open faces and chutes that holds pristine powder for days after a storm. The free snowcat will get you part of the way up, but the best lines require a 40-minute bootpack. The Deep Temerity area, serviced by a dedicated chairlift, holds a network of vertigo-inducing steeps, glades, and narrow chutes. Around 1 p.m., to unwind, eat fondue, and perhaps make some bad decisions, the Cloud 9 Alpine Bistro is always the move. This infamous on-mountain cabin is renowned for its decadent lunch service, where the malodorous fondue and raclette are followed by a boisterous champagne-soaked bacchanal. Just remember: you still have to ski to the bottom, and it’s a long, steep way down.
Back in town, the cultural offerings are as rich as the skiing. The Aspen Art Museum, a striking building designed by the world-renowned Japanese architect Shigeru Ban, hosts a year-round lineup of contemporary art exhibitions. The dining scene is no joke, with trendy spots like the Italian eatery Casa Tua, the seafood mecca Clark’s Oyster Bar, or Snow Lodge, Jayma Cardoso’s bumping people-watching perch.
Where to Stay
The long-awaited White Elephant Aspen will be the newest addition to Aspen’s luxury hotel scene when it opens in February 2026, primetime for Aspen skiing. A sophisticated and stylish retreat in the historic West End, the hotel will comprise 54 guestrooms and suites. The interiors follow the Nantucket brand’s signature palette of rich leathers, natural woods, and custom-made furnishings. And with the White Elephant comes LoLa 41, the sushi restaurant and infamous ACK pregaming spot, bringing that devilish Chad-and-Becky energy to the Rockies.
Telluride, Colorado
Photo: Getty Images
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