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At the tender age of nine, I vowed never to strap on skis again, after a single season of after-school lessons at Nashoba Valley Ski Resort in Westford. Gamely dressed in a one-piece snowsuit, I slogged over to the bunny hill and was horrified to be directed to a group of three- and four-year-olds. Apparently, I was already too old to learn to ski—kids my age were gliding effortlessly downhill while I was stuck with a bunch of preschoolers.

So what was I doing a few decades later, at an elevation of 8,000 feet, wedging my feet into a dense pair of ski boots? Well, Aspen, Colorado, has many charms, from a classic Western downtown to an exciting food scene, spas, hot tubs, and, of course, spectacular scenery. But foremost, especially on a bright, sunny winter day, is the skiing. The whole town is designed for it, from Aspen Skiing Company’s valet service, which will store your rental gear and transport it from mountain to mountain, to restaurants and bars that are only accessible on skis. Even the local art museum accommodates downhill fans, offering racks outside and slippers at the front desk to keep folks from tromping through the exhibits in ski boots.

Coming to Aspen and refusing to ski seemed like an affront to nature—so I broke my vow and set off to try at least two of the four mountains that compose Aspen’s skiing experience. To bolster my confidence, my first stop was to get some stylish gear. Twin brothers John and Pete Gaston started Strafe Outerwear in 2010, out of a passion for winter sports. With a shop and office at the base of Aspen Highlands, the brothers and their staff are laid-back and friendly—but very serious about skiing. On any given morning before work, it is likely that they hit the slopes at dawn for “skinning”—a strenuous activity involving hiking up a mountain and then skiing down—and they are happy to share favorite spots and expert advice with seasoned skiers.

I won’t be skinning anytime soon—I was just there for the confidence boost that comes with state-of-the-art gear, hoping that my new purple jacket and lightweight but super-warm coordinating pants would at least distract passersby from any lack of grace on my part.

From there, it was on to Buttermilk Mountain, which sounds gentle and easy, but actually offers a 2,030-foot vertical rise and is home to the X Games. Needless to say, my destination was not the longest run, which clocks in at three miles, but a “baby half-pipe”—a gentle downward slope that curves up after about 20 feet. The area was crafted for Aspen Skiing Company’s terrain-based learning—snow features designed specifically to help beginners gain skills. As Jo Archer, an instructor with Aspen Ski Company, explained, that upslope on the other side is intended to ease the terror that comes from your feet suddenly sliding downhill without you.

Archer assured me that she herself came late to skiing, and she specializes in adult learners. Perhaps it was Archer’s lilting South African accent, or the evident fear—far surpassing my own—in the eyes and posture of my fellow beginner, or that confidence-building hill that brought me to a slow halt after gaining a bit of speed, but my first day was pretty fun—although quickly exhausting.

Turns out the mountain views aren’t the only thing that is breathtaking in Aspen. For sea level dwellers like myself, the altitude is no joke—it can sneak up and leave you dizzy, parched, and with a terrible headache. It even affects sleep, and it’s impossible to predict who will fall victim—the most dedicated Crossfit fanatic can get altitude sickness just as easily as a couch potato.

The best cure is to move to a lower elevation—so I immersed myself in the heated outdoor pool at the Viceroy Hotel at the base of Snowmass Mountain, where I was staying. Surrounded by the Rockies’ towering peaks, the Viceroy is a chic ski-in, ski-out base of operations. Large guest rooms with sleek Art Deco décor offer lots of storage for bulky winter gear, along with a gas fireplace and amazing mountain views.

The resort is about a half-hour drive from charming downtown Aspen. Dominated on all sides by towering peaks, the downtown is still at a high elevation. Souvenir magnets say “Got Oxygen?”—a riff on the famous “Got Milk?” campaign—but it’s a great place to acclimate, starting with the Oxygen Lounge at the Remède Spa at the St. Regis Hotel. It may seem odd to recline on a posh chaise in a dimly lit room with tiny plastic tubes delivering straight O2 to your nostrils, but it diminished the near-constant throbbing headache that had been my companion since landing in Aspen. Recognized as one of the best spas in the world, in addition to a breath of fresh air, Remède offers steam caves, cold plunges, hot tubs, a fitness center, and a relaxing waterfall.

A short stroll from the spa brought me to the Aspen Art Museum, which moved into its stylish downtown space—meant to evoke a ski slope, of course—in 2014. One of the few noncollecting art museums in the country, the museum focuses on work by current artists who haven’t had a significant exhibition yet in the U.S. As such, the curators generally work with the artists themselves during installation, giving each new exhibit a personality and engaging perspective. The museum’s rooftop restaurant is no afterthought, serving up food-as-art in a beautiful space.

It’s not the only place presenting artistically plated food. Aspen has around 80 restaurants—far too many to name or to visit, unless you’re fortunate enough to be a local, or to be among the wealthy who have a second home here.  Two must-visit spots are noisy, buzzy Aspen Kitchen, serving up innovative food with creative presentation, and the elegant Element 47 at the storied Little Nell Hotel.

For those with some energy left after a day of skiing, Aspen’s nightlife is impressive, from a vibrant jazz scene to a big-name comedy festival. I stopped by the Hotel Jerome, where the eclectic décor pays homage to layers and layers of history, from references to ghost stories to a 38-star flag marking when Colorado joined the union. While the ephemera seem random, every piece tells a story from the property’s colorful past. Hunter S. Thompson considered the hotel’s J-Bar his office while working on stories for Rolling Stone. Toast the bar’s century-long history with an Aspen Crud—a vanilla milkshake enhanced with two or three shots of bourbon that was popularized during Prohibition. 

But go easy on the alcohol—it goes to your head faster, especially if you’re used to imbibing at sea level. Plus, whether a novice or a pro, you’ll want your wits about you to take advantage of Aspen’s perfect powder and amazing terrain. At least that was my thinking the next morning, when I boarded a gondola, then my first chair lift, at Snowmass Mountain. A stone’s throw from my hotel, Elk Camp Meadows, at an elevation of about 10,000 feet, is another terrain-based learning center, with “rollers”—a series of gentle up-and-down slopes to guide beginners through the basics of turning and stopping while caching a taste of the thrill of a real downhill run. With Archer’s steady encouraging patter in my ear, and the Rocky Mountains as a backdrop, I put snowplowing with preschoolers behind me at last. Look for me this winter at Bradford—I’ll be the novice hoping to distract onlookers with my really slick jacket.


Viceroy Snowmass Resort

130 Wood Road

Snowmass Village, Colorado