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Rediscovering Aspen Skiing and Nightlife

Mining village, countercultural hot spot, glamorous ski destination: find an intoxicating mix of arts, nightlife, and great skiing in Aspen.

By Julian Rubinstein

It’s around lunchtime in Aspen’s roaring Fork Valley, and I’d like nothing more than to tell you where I’m spending the afternoon. Only I can’t, because—as I myself have just accepted—I don’t know. I spent the past 40 minutes riding in the back of a Sno-Cat (fine) and then hiking (skis strapped to my back, but also fine) up the spine of a 12,392-foot peak. The so-called plan, known only to me, was to ski down the legendary Highland Bowl and then celebrate my accomplishment in, at minimum, a bar-serviced hot tub. This notion, however, appears to have been predicated on my live arrival at the summit, and as the panoramic Rocky Mountain–top view I had been enjoying disappears into a dark snow cloud, I soberly recall that my expedition began at the suggestion of an Aspen Timessex columnist whose dog, I knew damned well, was on the antidepressant Lexapro.

The wind whooshes and I steady myself with my poles, trying to enjoy the bitter cold. The thin ridge I’m ascending falls off so precipitously on either side that a few minutes ago, I couldn’t bear to look down. Now I have no choice. All I can see is my own lumbering ski-boot tracks. One unfortunate tilt to the left or right and the phrase early retirement takes on a whole new meaning.

Life-threatening was not what I had in mind when I planned my trip to Aspen. Then again, I was, upon my departure, between apartments and living out of a Manhattan Mini Storage unit. Aspen, I thought, promised something safe and familiar, a respite. It was a place I’d been going to since I was a child in Denver in the 1970’s. There were lots of beautiful destinations within striking distance, but Aspen, in the eyes of many Denverites, was not only the most picturesque mountain town around, but also the most authentic. Unlike resorts such as Vail or Breckenridge that were erected for ski tourism, Aspen has real history in the 19th-century American West. In 1893 it was the nation’s silver-mining capital, with six newspapers and a population of 12,000, when it went bust after the repeal of the Sherman Silver Purchase Act (which had briefly switched the country’s monetary standard from gold to silver). Remnants of that era still exist in the limestone buildings that line the downtown streets, and in the splintered Smuggler’s Mine chutes outside town where I used to climb.

As I became, by some measures, an adult, I continued to return to Aspen, and it was always the first place that came to mind whenever I was asked to name my favorite spot in the world. Usually I went in the summers, camping and hiking for several days in the shadow of the purple-hued Maroon Bells mountains, and then returning to town to partake of the wonders of plumbing and the excellent classical music put on by the Aspen Music Festival. Aspen, for me, was always a place of contrasts: rugged and pristine, sophisticated and simple.

But as the years went by, I began to notice that more and more people had their own opinions about Aspen, and invariably they were quite different from mine. While I continued to see Aspen as the eccentric, arts- and civic-minded town where Hunter S. Thompson once ran for sheriff, promising he wouldn’t eat mescaline while on duty, the wealth and celebrity Aspen had attracted since the days I started going—from Jack Nicholson to the Saudi Prince Bandar—created the impression that Aspen was like a Beverly Hills in the hills. The truth was, I thought, as my flight began its vertiginous descent into the snow-covered valley, I hadn’t been back in several years, and I had no idea what I would find.

When I stepped onto the tarmac, the late afternoon sun was bathing the valley in a pink-and-gold light. Behind me, the windows of the multimillion-dollar houses on Red Mountain glinted like diamonds. Along the edges of the airfield, snow was piled easily 10 feet high. This was a disquieting reminder that it had already been a historic ski season. (So much snow had fallen that the town had to hire trucks to cart it away. “I’ve been here 30 years and I’ve never seen a winter in which people actually said, ‘No more,’ ” Lon Winston, the director of the Thunder River Theatre Company, told me.) Disquieting, I say, because in my rush to get out here, I’d neglected to pack anything to ski in.

“Correct,” I said into my cell phone, to a man I’d been referred to. “Pants, gloves, hat, goggles, jacket. I have nothing.”

“No worries,” the voice on the other end said. “See you in fifteen minutes.”

I hopped the shuttle to my hotel on the outskirts of town, the Aspen Meadows Resort. A sprawling property designed in Bauhaus style, Aspen Meadows is best known as the home of the venerable Aspen Institute. Founded in 1950, the institute has—especially in the almost four years since its president, Walter Isaacson, inaugurated the Ideas Festival—vaulted to the top rung of world conferences, filling the town each summer with more VIP’s and plainclothes security men than an underground bunker during the apocalypse. Bill Clinton, the Dalai Lama, and Jordan’s Queen Noor are among the hundreds of luminaries who have passed through for public panels and talks under the same white tent that the Music Festival uses for its performances. When you throw in the Aspen Santa Fe Ballet, Jazz Aspen Snowmass, and the Aspen Writers’ Foundation, no place in the world remotely as small as Aspen (population 6,000) can boast such high-powered cultural institutions. I was pondering this outside the new and spectacularly designed Doerr-Hauser event and art space when a Jeff Spicoli–style van pulled up in front of me, and out jumped a sunburned, long-maned man wearing ski pants and a black turtleneck. “Sorry I’m late,” said Lorenzo Semple III, 41, shaking my hand. “You caught me right as I was coming off the Bowl. Absolutely epic.” He slid open the van door, revealing two hanging racks of ski apparel. “Suit Yourself,” he said, stating the name of his business. Aha, I thought: I’ve arrived.

As I assembled an outfit, Semple and I covered an array of topics I’d never found so riveting—for example, lawn mowing, which he does all summer. Semple was dramatic in a good way, a true enthusiast, and it didn’t surprise me to learn that he is the son of legendary screenwriter Lorenzo Semple Jr. (Three Days of the Condor), the man he calls “my hero,” and who first brought him to Aspen more than 30 years ago. Semple still has some Hollywood in him—he ended a cell-phone conversation with a phonetic kiss, “Mwah”—and I couldn’t help but think he perfectly embodied the grit and glamour that make Aspen so unique. “I have two religions,” he said. “Mountain biking and skiing. This year my goal is to get 200 runs on the Bowl. So far I’m at 152.”

Everywhere I went, people were talking about “the bowl”—which, in an outdoor fantasyland like Aspen, is nothing to shrug off. Ice climbing, ice fishing, snowmobiling, cross-country skiing to a mountain chalet—it’s all here. Plus, Aspen is one of the only resort towns in North America with four separate ski mountains, 5,285 acres of terrain, all of it world-class. But the Highland Bowl—on Aspen Highlands mountain, a free 10-minute shuttle away from town—is one of the largest bowls in the world that is entirely “in bounds,” meaning that it is maintained by the ski patrol. It had only fully opened in 2002, after I’d last skied Aspen, and I knew this time I would have to take it on.

That night I rode into town. Strung over Main Street was a colorful banner advertising the week’s events: the Junior National ski races, a concert by pianist Stephen Hough, a reading by Pulitzer Prize winner Richard Russo, and the public radio fund-raising drive. I hopped out at Galena Street and walked toward the historic Elks Building in the center of town. Window after storefront window gleamed with shiny jewelry and designer clothing: Zegna, Gucci, and Dior, all staking their sidewalk claims. The old Ute City Pub I used to love was now, to my dismay, a Burberry. Still, it was all but impossible to be depressed. Though it had been snowing on and off and the temperature was in the twenties, the dry air was crisp and invigorating, and the scenery in all directions—the mountains, the valley, the cozy lamplit streets—was simply staggering. “You know, just another day in paradise,” I overheard a man saying on his cell phone as he passed me, and I found myself nodding hello.

I had dinner plans with an Aspen fixture named Tim Mooney, who had chosen the low-key Topper’s Aspenrestaurant, a small, warm joint off the beaten path that serves pasta and brick-oven pizzas. When I arrived, he was at a table in back, shaking his head at an item in the Aspen Daily News police blotter. (My favorite during my stay: Stranger Found Sleeping in Aspen Home.)

Mooney had a story like those of many residents I met. He arrived in Aspen in 1970 during a stopover on a road trip and never left. Since then he’s had many careers: he was a tour manager for Aspenites John Denver and Jimmy Buffett; he was a ski instructor for 23 years (and served for many of them as Jack Nicholson’s private teacher) until he was famously fired in 2001 for chainsawing trees on the mountain to make a new ski trail. In his honor, residents now call the run “the Dark Side of Mooney.” In his latest incarnation, Mooney is a real estate broker with Sotheby’s, which he admits “isn’t the best way to make a living at the moment.” But despite the downturn, the average home price in Aspen is $4.3 million; a $40 million spec house is being built on Red Mountain; and at Aspen’s sister mountain, Snowmass, a colossal $1.3 billion new base development—nearly a million square feet of new condos, houses, commercial spaces, and time-shares—is set to open this year. “The incredible power of this little town,” Mooney said, shaking his balding head and putting back a Merlot. “About fifteen hundred people vote in Aspen. Last year there was $2.5 billion in real estate transactions.”

We talked about how much had changed since the time both of us began coming here more than three decades ago. Back then, about a hundred babies per year were delivered at Aspen Valley Hospital; now the average is more than 300. Growth and development had always dominated local politics, and in that regard, nothing has changed—at least nothing for the better, in Mooney’s view. “We used to have a mom-and-pop ski town with old European-style hotels. Now, we have these new parked cruise ships at the base of Aspen Mountain,” he said, referring to the luxury hotels that have opened in the past several years. Mooney believes a setback in the battle against overdevelopment was the death in 2005 of long-time Aspen resident and activist Hunter S. Thompson. When Thompson was alive, Mooney and a group of regulars met weekly in Hunter’s kitchen at Owl Farm, in what many describe as “the command center of Aspen politics.” There they strategized about how to keep out what Thompson called the Greedheads, and limit development. In 1995, for example, the group successfully campaigned to prevent 737’s from flying into the airfield—today there are more than 150 commercial flights per week but no 737’s—using a now-celebrated campaign poster designed by the late artist Tom Benton, with the slogan There is Some Shit We Won’t Eat.

Now there’s a new fight brewing over the expansion of the airport runway. “Hunter would have been vicious about this,” Mooney said. “We lost the most powerful voice there was standing up for the little guy against big business.”

While we were eating, his phone rang. It was his friend, painter Paul Pascarella, another Thompson pal, who was coming to town for an exhibition of his work at the Magidson Fine Art Gallery, one of the dozens in Aspen that feature artists of national repute. “That’s the funny thing about this town,” Mooney said. “I don’t need to go to New York or Los Angeles to find out what’s going on. They come to me.”

I spent the next several days living so far above my means I almost expected to be arrested, which may not have been entirely unfortunate. I was, after all, homeless, and the Pitkin County Jail, I learned from the riffraff I was carousing with, has beautiful views, great meals, and free painting classes offered by Aspen artists. (One of the town’s most recent soap operas was the re-election of local icon and sheriff Bob Braudis to his sixth term, never mind that he campaigned for a time from an alcohol rehab center.)

I skied the fresh powder on Aspen Mountain, or Ajax, as the locals call it, and had one of the best meals of my life at Montagna, inside the luxurious classic Aspen ski-in, ski-out hotel, the Little Nell. There, 34-year-old wunderkind chef Ryan Hardy, a southwest finalist for the 2008 James Beard Awards, lists his olive oils on the menu like wine, and cooks up his delicacies with produce and meat—I devoured a juicy lamb sausage with rapini and mustard—from his own nearby organic farm. Another night, I went out to the Richard Russo reading at the Given Institute, a state-of-the-art conference center nestled into the oldest residential neighborhood in Aspen, where many of the homes still have the old Sears-catalog frames. Inside, the lecture-hall setting was formal—“Thank you for inviting me to the UN,” Russo joked when he took the podium—but the feel of the event was small-town tea party. Ski instructors, restaurant managers, former mayor Helen Klanderud, and others gabbed in the atrium before the event.

Afterward, a big group flocked through the snowy streets to the Victorian home of Lois Smith Brady, frequent author of the popular New York Times Vows column. A small, quick-witted blonde with a generous wine pour, Brady wove her guests together, and by the end of the night I found myself with her, Russo, and several others in the kitchen, all of us but Russo pledging to do the Bowl together later in the week. I tottered back to my hotel and, entertaining notions of missing my return flight for the next several years, decided to take a ride “down valley” the next day, where the area’s most rapid development has been taking place.

The ripple effect of Aspen’s eminence and high price tag has kicked off the gentrification of formerly low-income, mostly Hispanic towns like Basalt and Carbondale, which today have nearly $1 million average home prices and attract people from all over the country. Aspen residents now head to Carbondale the first Friday of each month for the First Fridays Art Walk, in which the whole downtown is closed for gallery openings, and parties pour into the streets. Architect Michael Lipkin had a major impact on the area’s development, founding and building a planned community called Willits. Twenty-two miles from Aspen, Willits is a New Urbanist town similar to Florida’s Seaside, which was created by classmates of Lipkin’s from the Yale School of Architecture. “The concept was to develop a community where everything is within walking distance,” said Lipkin, who moved to Aspen from Manhattan in the 1980’s.

Willits now has 1,800 residents, and represents a brand of sane and sustainable development. There’s a lake, soccer fields, and a running path winding through a long park. At its end is a traditional gridded “downtown”—complete with a general store serving gourmet sandwiches and sporting on its brick façade a fading painted replica of an award-winning Conoco ad from the 1950’s. Next door is a strip of restaurants, above which sit two floors of New York–style loft apartments with million-dollar mountain views. Among them is the stylish Nouveau American restaurant Crave, which stole its chef from Aspen’s venerable Hotel Jerome.

I would have stayed, but I had dinner plans back in Aspen at a new restaurant called Social. Situated in the same downtown building as long-standing Aspen favorite Elevation, Social is also owned by the same team, which includes Gunnar Sachs, son of legendary international playboy Gunter Sachs. A sleek lounge with banquettes, silver globe chandeliers, and a floor-to-ceiling wine rack sitting behind a glass wall, Social serves tapas-style plates—the Kobe meatballs, Boursin-cheese mashers, and caramelized-onion jus were just the ticket for me. Social’s affable manager and co-owner Denise Walters—a wicked snowboarder who just completed her third move to Aspen, this time from New York—then took me downstairs to Elevation, where we continued to eat, and drank an açai martini that’s so delicious the bartender has to hide the Brazilian nectar because the staff keeps sneaking off with it.

All around us, people were talking about where to go next. Some were heading to the bar at Matsuhisa, the Nobu restaurant owned by billionaire Aspen resident Michael Goldberg. I’d been hearing about Goldberg’s three-year-old music club, Belly Up Aspen—the town’s first contemporary-music dance venue, which brings in world-class acts (MSTRKRFT, Seal, Cake) year-round. Just then my phone rang. It was Mooney, who was having a drink a few blocks away at Pacifica Seafood & Raw Bar. When we got there, the painter Pascarella, a bearded man with a knowing smile, was being toasted on the occasion of his gallery opening. More martinis were had until someone at the bar, recognizing Mooney, came over and offered us tickets to the show at Belly Up. Minutes later we were there, thumping along to the strobe lights and electronic music. In the corner above the dance floor, tucked into the back of the booth, was Goldberg himself, a giant of a man (his brother is the hulking pro wrestler known simply as Goldberg), surrounded by beautiful women.

The place was still rocking around midnight, but I had to be up in a few hours. I was going to meet Mac Smith, the head of the Aspen Highlands Ski Patrol.

The sky was dark when my alarm went off. I checked my e-mail to find that Lois Smith Brady and the others who had promised to join me on the Bowl had canceled. I dressed and stumbled into the Highlands shuttle.

The streets were almost empty, the lights from the Sno-Cats the only visible movement on the mountain. I made my way to the bowels of the Highland base building, following the smell of coffee to the patrol conference room. About 20 people—varying in age from their twenties to fifties, all but three of them men—were gathered around, buckling their ski boots and eating muffins. These were the elite of Aspen, the chosen few who survived Mac Smith’s infamous boot camp and were then selected for the most highly regarded patrol in Colorado.

Smith has a huge gray walrus mustache and long eyebrows, one of which turns up and the other down. At exactly 7:55 a.m., he strode into the room with a long lope and leaned against the back wall. Soft-spoken but businesslike, he jumped straight into a rundown of fences and signs to mend, and a follow-up report on a “lost missing person yesterday,” who was found and then somehow lost again. Then he turned it over to his staff snow-and-weather expert, a barefoot, gnomelike man with a ZZ Top beard and taped toes, who spoke for nearly half an hour about trade winds and pressure systems, then finished by saying, “That’s about all I have.”

“Okay, let’s go,” Smith said, and within a minute the room was empty.

I rode up the lift with Smith, a native of Basalt, who was monitoring the radio strapped around his chest the whole way. When I asked him about the history of the Highland Bowl, he surprised me by getting emotional. He tried to open it first in 1984, but three of his patrolmen were killed while purposely triggering an avalanche. It took him four years to get back the strength to attempt the challenge again. On the day the Bowl opened, he laid three wreaths for his friends. “It’s kind of like a dream you don’t know will ever come true,” he said. There have been no deaths since.

When we got to the top, we skate-skied over to the patrol station, a solar-powered cabin hovering on wood stilts. Soon a drill was being organized to train two black Labrador “dog techs” to rescue avalanche victims. With a devious smile, Smith suggested I volunteer to get in “the hole,” to which I first agreed, then changed my mind after seeing the tiny chamber six feet under I was going to be buried in. While Smith laughed, I took up a shovel and helped bury two rookie patrolmen. The dogs had never been tested before on the mountain but within a minute of being set loose, they had located by scent both sites, and stood barking above them.

Finally, it was time to do the Bowl. I put on my helmet and goggles, and strapped my skis onto my back. “Good luck,” Smith said, as I headed to the Sno-Cat that would take me up the first third of a mile of the two-mile hike.

The sky was just beginning to cloud over as I got off the cat and began my ascent. Within 20 minutes, there was no trace of life around me. My world had been reduced to wind. I remembered how Smith had told me he’d used more than 10 times the amount of dynamite to control the snow this year than he ever had. I’d also been told how Aspen resident Neal Biedelman, a world-renowned mountaineer who survived Everest with Jon Krakauer, had nearly been buried alive earlier in the season while skiing out of bounds. (For the record, Aspen would finish the season with 510 inches of snow; the average per year is 300. For the first time in history, it opened for an encore day of skiing in June.) That’s it, I thought as I stepped blindly into thin air, this is my Everest.

Then I heard a noise. Someone was coming up behind me. I looked over my shoulder to see Semple. “Right on,” he said, giving me a thumbs-up and hoofing by. Even as he disappeared into the cloud ahead, I knew then that I’d be okay. When I reached the summit, the sky began to clear and I stood gasping at the 360-degree view. At last one thing was wonderfully clear: as disparate as the interests and impressions that define Aspen are, the staggering physical beauty of the place was the reason they existed at all. Minutes later, I was knee-deep in champagne powder and falling once again for the town I knew and loved.