Discover Aspen, Colorado’s most glamorous ski town.
Aspen’s trajectory from silver mining town to one of the most recognizable luxury resort addresses in the world is not, strictly speaking, a story about skiing. It is a story about reinvention, about the particular alchemy that happens when serious money, serious culture, and extraordinary natural surroundings occupy the same small mountain valley.
The skiing helped, obviously. But plenty of ski resorts have good skiing. What Aspen has that most of them lack is a sense of itself: an identity that has been building since the 1940s and shows no sign of fading.
The Backstory
Aspen was a silver boomtown in the late nineteenth century, briefly one of the largest cities in Colorado, before the crash of 1893 left it largely empty. It drifted quietly for decades until Walter Paepcke, a Chicago industrialist with a philosophical bent, arrived in the late 1940s and decided to build something.
His vision was not a ski resort in the conventional sense. It was a place for ideas, for culture, for what he called the renewal of mind, body, and spirit. He founded the Aspen Institute, brought in intellectuals and artists, and opened the first chairlift on Aspen Mountain in 1947. The Aspen Music Festival followed in 1949 and is still going. The blueprint he laid down, serious outdoor recreation combined with serious cultural programming, is still the template the town operates on today.
The celebrities arrived later and have never really left. Hunter S. Thompson lived here. Jack Nicholson had a house here. The roster of regulars over the decades reads like an extended exercise in name-dropping: the Kennedys, Goldie Hawn and Kurt Russell, Kevin Costner, Mariah Carey, and a rotating cast of tech billionaires and hedge fund managers who have quietly made Aspen real estate some of the most expensive in the United States.
The town’s permanent population is under 8,000 people. The concentration of wealth per square mile during peak weeks in December and January is difficult to overstate.
We Suggest...
Aspen in Winter: A Luxury Gay Ski Escape
Tailor-Made VacationAspen is one of those places that rewards arriving with no particular agenda. It’s one of the top luxury travel destinations in the USA. The skiing across four mountains is as good as anywhere in North America, but the town...
When to Go
The social calendar has a logic of its own. Christmas and New Year are when the town reaches full intensity, with Pitkin County Airport handling a concentration of private jets that ranks among the busiest in the country for those two weeks.
Restaurants require reservations made well in advance, the mountain is busy, and the energy in town is high. Presidents’ Day in February is the other peak.
January is the connoisseur’s choice. The same mountains, the same hotels, the same restaurants, but with a slightly lower social temperature that many regulars actively prefer. The snow is often at its best, the lift lines shorter, and the town slightly more itself without the holiday pressure.
Summer has developed into a genuine second season. The Aspen Music Festival runs through June and July, the Food and Wine Classic in June draws a serious culinary crowd, and the hiking in the Elk Mountains is exceptional.
The Maroon Bells, two fourteeners reflected in a glacial lake just outside town, are among the most photographed landscapes in the country. Fall, when the namesake aspen trees turn gold across the mountainsides in late September and early October, is the quietest and some would argue the most beautiful time of all.
The Hotels
Three properties define the upper end of the Aspen hotel market and between them cover most traveler types.
The Little Nell is the one most visitors aspire to. The only ski-in, ski-out hotel in Aspen, it sits at the base of the gondola with the kind of position that cannot be replicated. The rooms are warm and residential rather than flashy, the service has the ease of a property that has been doing this for a long time, and Element 47, the in-house restaurant, is one of the better places to eat in town regardless of where you are staying. The wine program is exceptional. It is expensive and worth it.
The St. Regis Aspen sits a short walk from the slopes with a more contemporary aesthetic and a spa that is genuinely among the finest in Colorado. The Remède Spa runs across two floors and does the kind of treatments that justify building a recovery afternoon into the itinerary. The rooftop pool in winter, heated and open against a backdrop of snow-covered mountains, is one of those experiences that photographs poorly and delivers completely.
Hotel Jerome is the historical anchor. It opened in 1889 at the height of the silver boom, survived the bust, and reopened after an extensive restoration as part of the Auberge Resorts Collection. The J-Bar downstairs is a Aspen institution, a proper après ski bar with a sense of place and history that the newer properties cannot manufacture. If you want to understand what Aspen actually is, rather than what it has become, an evening at the J-Bar is as instructive as anything else in town.
On the Mountain
Aspen Snowmass operates four mountains: Aspen Mountain, Snowmass, Aspen Highlands, and Buttermilk. Together they represent one of the most varied ski areas in North America.
Aspen Mountain is where the town skis. No beginners’ terrain, direct gondola access from downtown, and a layout that rewards exploring. Snowmass is the largest of the four, with a wider range of terrain and a self-contained base village that feels like a resort within a resort. Aspen Highlands is where serious skiers tend to gravitate: the Highland Bowl, reached by a 30-minute hike from the top of the lift, is a genuine backcountry experience within a lift-accessed ski area. Buttermilk is quieter and gentler, and tends to be underrated.
A private ski guide transforms the experience regardless of ability level. They read the mountain, manage the logistics, and take you to places you would not find independently. For a first visit especially, it is money well spent.
Off the slopes, a snowcat dinner in the backcountry is one of those experiences that justifies the trip. A grooming vehicle takes a small group up into the mountains after dark for a private dinner in a yurt, with the lights of the valley visible far below. It sounds gimmicky in description and is not at all in practice.
The Food Scene
Aspen’s restaurant culture is disproportionate to the town’s size, sustained by a clientele that eats well at home and expects the same when traveling. Matsuhisa, Nobu’s Aspen outpost, has been operating here since 1998 and remains one of the most consistently good restaurants in town. Element 47 at the Little Nell is the formal option worth the occasion. Casa Tua operates more like a private supper club than a restaurant and requires knowing someone or booking well in advance.
White House Tavern is the best option when you want something excellent without the effort. Betula, which opened more recently, represents some of the most considered cooking in Aspen and is worth seeking out.
Gay Travel in Aspen
Aspen has a quietly inclusive culture that predates the current conversation about LGBTQ+ travel by several decades. The town’s cosmopolitan makeup and long history of liberal politics mean that same-sex couples travel here without issue and have done for years.
There is no defined gay neighborhood or bar scene in the way that Palm Springs or Provincetown have one, but the social environment across the major hotels and restaurants is genuinely indifferent to who you are traveling with.
The specific reason to put Aspen on the LGBTQ+ travel map, however, is Gay Ski Week. Running every January since 1976, it is one of the oldest and largest LGBTQ+ ski events in the world, attracting thousands of visitors from across the US and internationally for a week of skiing, parties, and events that take over the town in the best possible way.
The main hotels fill up fast for those dates. If your schedule is flexible and you have not been, it is worth building a trip around.
Out Of Office builds tailor-made Aspen itineraries for all seasons. Talk to our team about what a winter escape, summer hiking trip, or Gay Ski Week visit might look like for you.
