Like Youth, Are Gap Years Wasted on the Young? My Super Sabbatical

I always wanted to take a Gap Year; it took me decades to do so

I always wanted to take a Gap Year; it took me decades to do so

Maybe it’s the travel year abroad that I wanted but never had—before, during, or after college—that made me obsessed for decades with the idea of taking a gap year.

But I put that yearning on the back burner when I left the East Coast in my early twenties for adventures in the American West, parts of which were still pretty Wild back then. Long before people buzzed about follow your passion, my husband Randy and I followed our dream and moved to Aspen, Colorado in 1987 to start Aspen Magazine, and live the mountain life.

Many of our college friends lived in Manhattan and had traditional jobs in publishing, finance, law. While our city friends often said they wish they could trade places with us, they weren’t willing to take the risks we took. And risks there were. While iconic, Aspen back then was more funky small town than glamorous St. Moritz. Outside of seasonal jobs like ski instructing or waiting tables, jobs were few. We weren’t trust funders like many of our friends there. Our families thought we were crazy.

I served as the magazine's Editor in Chief, and my husband as Publisher. We played hard, but we worked hard too. In my forties, I tried to plan a short sabbatical in 2000 to write and gain some mid-life perspective. As fate would have it, that year my life was turned upside down. Out of the blue my healthy, athletic husband was diagnosed with stage four Non-Hodgkins Lymphoma. Within a year he was dead.

What an emotionally, physically, and financially draining year it was. Devastated, I desperately needed time off to grieve. But with a small business to run and medical bills that went beyond our insurance coverage to pay, there was no time off; there wasn’t even time for a mid-life crisis. 

After my husband's sudden death, I took on even more roles, without shedding old ones. Business was good until 2007 when the great recession collided with the digital revolution—two forces beyond my personal control.  Despite stereotypes of the town’s wealth, Aspen was not immune to the recession. I had created a great brand, but with the steep decline in print advertising revenues, the print magazine business for most publishers, especially small ones like ours, was daunting; many small publications were forced to close. By the end of 2012, for a variety of reasons I was more than ready to sell. 

I’d experienced an adventurous, satisfying 25 years of doing my dream job in a place I love. I cut my three year contract with the new owner to one year. I was ready to hit the slow button. I took on a few freelance projects, renovated my home, skied, biked, hiked—and went under the social radar.

Then on a trip to my sister’s in the Midwest, I was shocked when she described me as “retired.”

I was shocked by the word “Retired”

I was shocked by the word “Retired”

The word “retirement” comes from the Middle French word retirer, meaning to retreat, to withdraw, to go off into seclusion. Up until the 18th century, people worked until they died, either on a farm, or for the rich, managing their estates. The idea of retirement was invented in Germany in the late 19th century. In the U.S. pensions for municipal employees were introduced in the 1880s, and eventually offered across industries, with 65 the official retirement age. 

From its inception, the notion of retirement aligned with life expectancy. These days the 20th century idea of retirement as a macro event is in full disruption. As Business Insider recently put it, the notion of retirement as a one time event of ceasing all work—"you’re born, go to school, get a job, retire, die" is obsolete. In the 21st century, life expectancy will now most likely be extended: it's mind boggling to think we might live to 110 or 120. 

I may be done with my career in traditional publishing, I thought, but I wasn’t retired from storytelling or living life to the fullest. But before I could begin any new chapter I was finally going to take—whatever you want to call it—that adult gap year, that super sabbatical, that mini-retirement, that time out for creative personal projects and travel that I had always dreamt about. 

Though I made my decision to take an extended sabbatical years ago, according to Conde Nast Traveler a new travel trend is burned-out billionaires “turbocharging” the idea of a gap year. One tech entrepreneur travelled for two years by private jet to 66 countries, spending in the seven figures. He even lived for two weeks in the Kalahari (where I have explored) with the San and hunted animals with a bow and arrow with the tribespeople. He had the means to hire an Emmy Award-winning cameraman and BBC guide to make a documentary of his exploits.

My super sabbatical has been less grand than those cited in the CNT story, and certainly less expensive, but nevertheless I created the break from burnout and the time and space for personal transformation that I was seeking. To the surprise of my friends and family—and even myself—I moved, just for a year I said, to do a deep dive of my favorite city, Manhattan, which I had only known as a tourist in hotels or a friend’s guest room.

Being my own boss most of my adult life I am a self-directed learner and doer. Rather than go back to school, which I had considered, I made the City’s cultural offerings—museums, jazz clubs, classical music, opera, theatre, talks, and architectural tours—my classroom. I invested in a Sony digital camera and became a flaneur. And I traveled constantly. Though I was technically not adept, I went on photo workshops in India, Oaxaca, Ireland, which stimulated me to take photography classes later in Manhattan. I now have a new passion that adds endless value to my life and work.

These days my personal hashtag is: #rewiredontretire. I wish I could claim credit for coining the term, but I discovered it in the book Wisdom @Work: the Making of a Modern Elder by hospitality entrepreneur and marketing guru Chip Conley.  Some people don’t like the word “elder,” but it's definitely not the same as elderly. 

A book with valuable insights about aging and youth

A book with valuable insights about aging and youth

The book looks at growing older while staying younger. The author makes the case for wisdom not being wasted on the old any more than youth being wasted on the young. Age diverse workplaces are smart business, an idea that fascinates me and I hope we’ll see more intergenerational work models in our society.

And speaking of youth, millennials are already clueing into the boomer new reality of working longer. Eighty percent plan continued employment beyond 65, according to Money magazine. But millennials are also being smarter than my generation in seizing upon the idea of adult gap years, or "mini-retirements"—meaningful respites throughout one’s career to get more out of life. The concept was conceived and popularized by author Timothy Ferris in his book The Four Hour Workweek, published in 2007. 

Those living longer will want to participate in the economy—either because you financially need to, or you have made the choice to stay useful and purposeful. Stories abound of people who remain active and happy by doing work they enjoy into their 70s, 80s, and beyond.

With new ideas about youthful aging and work paradigm shifts in mind, Conley’s even started a school in Baja, Mexico—the Modern Elder Academy—to help one “to reset, restore, and repurpose your life” during life/work transitions. Universities like Stanford and Harvard for instance offer programs for boomers looking to reinvent second or third acts with new direction.

So here I am, starting back to work with my blog. I’ve come to realize that nothing’s ever wasted at any age when you take time out for renewal and experiences that take you out of your comfort zone.  As my extended Gap Year comes to a close it’s made re-rethink my notions of time, age, work, and what I’m capable of. Endings are never quite what they seem. Or as Meister Eckhart once wisely said: “And suddenly you know: It’s time to start something new and trust the magic of beginnings—” even if you have turned 65.



It’s SNOW time! Get your SKIS and BOARDS out

Photo courtesy of the Aspen Skiing Company

Photo courtesy of the Aspen Skiing Company

It's true, Aspen conjures up images of wild partying and decadence. And it's definitely a destination for swipe-right singles. But that's not why I, and many others, love this town. For Aspenphiles, there’s something about Aspen that makes it the perfect place to go beyond your comfort zone. To go adventuring. To challenge your mind, body, and, yes, spirit—even on a ski vacation. 

Photo courtesy of the Aspen Skiing Company

Photo courtesy of the Aspen Skiing Company

Photo courtesy of the Aspen Skiing Company

Photo courtesy of the Aspen Skiing Company

For many returning, long-time skiers it’s also comforting that Aspen doesn’t seem to have changed beyond all recognition over the years. Beloved landmarks still greet you, like the Hotel Jerome, the Wheeler Opera House, The Brand Building, Collins Block, and the lovingly restored Victorians in the West End. But many locals will object that of course Aspen has changed dramatically. Especially the downtown, with real estate prices as steep as the slopes. The resort mostly attracts the Ultra Rich and their offspring, though resourceful millennials of lesser means still manage to attend the action-packed X-Games in January, when rates are lower. 

Photo by Janet O'Grady

Photo by Janet O'Grady

Since its founding during the 1890’s mining era, Aspen’s always attracted the wealthy. After the silver bust of 1893, the town was almost abandoned as ranching took over, and then was rediscovered and reinvented in the late 1940s by the patrician Chicago industrialist Walter Paepcke and his wife Elizabeth. In addition to captains of industry, Aspen’s long attracted rebels, from Wall Street dropouts who became ski bums to gonzo journalist Hunter S. Thompson. You may want to meet some of those eccentric ski bums, but I'm sorry, they're not really here any more. But you'll still find celebrities from time to time, like Diana Ross, Johnny Depp, Uma Thurman, Mariah Carey, as well as the Clintons, and Michelle Obama and daughters. Goldie Hawn and Kurt Russell, who own an Old Snowmass ranch, are mainstays, often seen walking around town with Kate and Oliver. And then there’s also the entrepreneurs and tech titans of recent years, like Virgin’s Richard Branson, Starbucks Howard Schultz, and Amazon's Jeff Bezos. 

Photo courtesy of Aspen Skiing Company

Photo courtesy of Aspen Skiing Company

But don’t expect to see the bold-faced names on the party circuit. Much of what happens in Aspen takes place behind closed doors. The operative word is private.  

Nowadays it seems as if many visitors focus less on the skiing and more on the shopping—it’s world class— and gawking at the private jets (if they didn’t arrive in one), the mansions of Red Mountain and Starwood, and the bling and fur that fill the town, especially during Christmas and New Year's.

But for many visitors, and long-time locals like myself, we’re here for the skiing. Here’s my own mini guide —hardly meant to be inclusive; welcome to Aspen in winter.


Many first timers don’t realize the destination includes four mountains in one place, all accessed with one arty (contemporary artists create original images) lift ticket: Aspen Mountain; Aspen Highlands; Buttermilk; and about 10 miles from town, Snowmass. Each has its own personality. All are operated by the Aspen Skiing Co, owned by Chicago’s prominent Crown family. With a total of 336 trails and 5,517 acres, that's a lot of variety. 

Photo courtesy of the Aspen Skiing Company

Photo courtesy of the Aspen Skiing Company


Nicknamed ‘Ajax’ after a former mine, Aspen's famous for its flash and flair. But with 65% of its trails rated expert, and no beginners’ terrain, these slopes require solid intermediate to expert skills. A gondola whisks you from the base at 7,945 ft to 11,212 ft in about 14 minutes; you can squeeze in so many runs that your quads get a real workout.  

Less than half the mountain is visible from town; what you're looking up at is the iconic Ridge of Bell. The mountain offers so many adrenaline rushes, from the steep pitches of the Mine Dumps to Walsh’s. Ruthie’s—named after a historic Aspen character—is an intermediate pleaser. Non-skiers should purchase a gondola pass and have lunch at the Sundeck; the awesome views rival the Swiss Alps. 

Bonnies on the mountain is my favorite eatery, famous for its white-bean soup and apple strudel, and, over the years, Jack Nicolson sightings. I love hanging out on its sun-drenched deck.

Photo by Janet O'Grady

Photo by Janet O'Grady

Aspen Highlands  

Photo courtesy of the Aspen Skiing Company

Photo courtesy of the Aspen Skiing Company

Photo courtesy of the Aspen Skiing Company

Photo courtesy of the Aspen Skiing Company

Baddass Highlands is where the hard core flock. Ranked amongst Colorado’s steepest, its 1,040 acres of vertical range from cruisers to double-black diamonds. Visually, the area’s stunning, especially the knock out views of neighboring Maroon Bells and Pyramid Peak at its 12,392 ft summit. Steep gladed trails lie off the mountain’s long spine, making for great powder days. More than a third of the terrain is rated double-black, including the legendary moguled Steeplechase. But the real star is the off-piste Highland Bowl—simply called the Bowl—where your turns earn you bragging rights.

Photo by T.J. David/Courtesy of the Aspen Skiing Company

Photo by T.J. David/Courtesy of the Aspen Skiing Company

A snowcat takes you about a third of the way, and then, shouldering skis or boards, you hike the rest; depending on your fitness level and acclimatization, it can take a half hour or more. But the walk’s worth the views. And skiing the thrilling 2,500 vertical feet—slopes vary in pitch from 38 to 48 degrees. You're within the official ski area, but you definitely feel out of bounds!

Photo by Janet O'Grady

Photo by Janet O'Grady

I love Cloud Nine Alpine Bistro, everyone loves Cloud Nine, an Aspen institution that lives up to its name. After finishing your raclette, you just may find yourself dancing on table tops, while joining fellow revelers spraying one another with Veuve Clicquot. Really. It's an Aspen tradition. You must ski well enough to get to this Euro-style eatery, housed in a former ski patrol log cabin, and ski well enough, Champagne and all, to get down afterwards. (Dinners are also offered but you travel via snowcat). Last year's makeover and expansion got it right. Inside's still cozy but now opens on to even bigger views of the Maroon Bells. Vintage ski photos line the walls, patrol sleds hang from the ceiling, all a tad Ralph Lauren. 


Photo courtesy of the Aspen Skiing Company

Photo courtesy of the Aspen Skiing Company


As its name suggests, this mountain’s massive. With 4,406 vertical ft and more than 3,332 acres surrounded by national forests, it’s also bigger than the other three mountains combined. While best known for beginner and intermediate slopes, Snowmass is also home to some thrilling extreme terrain, like Hanging Valley Head Wall, Gowdy's, and the Cirque, reached by old fashion platter tows that transport you to 12,510’—with spectacular views of the Maroon Bells and Snowmass Mountain. But mostly I love how everyone feels like a star at Snowmass, especially on cruisers like Naked Lady, and the five-mile intermediate Long Shot— set amidst glades and trees— and one of the longest runs in North America. Check out other fantastic blues (intermediate) like Big Burn and Sheer Bliss. The area offers lots for families too, especially its 25,000 square foot Treehouse venue, with excellent programs for kids ranging from 8 weeks to 14 years old. And several good on-mountain restaurants, with Elk Camp my favorite. In 2010 fossils of Ice Age animals —mammoths and mastodons— were found nearby, and are on display at the the Discovery Village on the village mall. 


If there’s such a thing as nursery slopes in Aspen, here they are. It's a mecca for children who adore the Fort Frog play park here. It’s also a mecca for adult beginners. And a paparazzi-free zone for the many celebrities who hit these bunny slopes. Home to the X Games, the mountain is loved by boarders for its terrain parks. And everyone loves the longer runs off its West Buttermilk high-speed lift. Tiehack, the slopes to the east, offer sweeping vistas of dramatic Maroon Creek Valley. It’s also many a local’s favorite on powder days, since the powder doesn't get skied off as quickly as other mountains. 

PHONE: 970/925-1220 or 800/525-6200.   aspen snowmass


Life's too short to ski badly. Lessons are a great investment in yourself, and Aspen/Snowmass runs one of the best ski schools in the world. Learning to conquer things we once felt we couldn’t do, or ski with more flow and finesse, is an integral part of getting out of your comfort zone.  Opt for more affordable group, or pricier private lessons. 

Imagine having Aspen Mountain all to yourself? Well, that’s First Tracks. Sign up the day before, load the gondola before the crowd, and ski down on empty slopes, as if it’s your own private mountain. 

Adventure off piste by snowcat to the back side of Aspen Mountain with Aspen Mountain Powder Tours. Compared to the costs of hell-skiing, these excursions are bargains. Guests of The Little Nell hotel can even sign up for full moon private powder tours. 

Former World Freestyle champion John Clendenin’s two-and three-day camps offer instruction from pros trained in his Ski Method, which focuses on skiing moguls with more grace and flow. In addition to on slope instruction, expect daily video analysis, fun parties, and other perks. A camp is also offered in Val d’Isere, France. 

The Little Nell’s Click-in with legendary pro skier Chris Davenport February 6-10; it's definitely on my bucket list. The Nell offers excellent experiential programs, the best in town, and this is the winter version of its summer cycling camp with bike pro Christian Vande Velde. In three days you’ll learn about the area's mountains, improve your skiing, and have a blast during special aprés, dining, and evening events. 


There are Little Nell Hotel junkies, and I’m one of them. What’s not to love? The Silver Queen Gondola's just footsteps from Aspen’s only ski-in/ski-out five-star property. Holly Hunt redesigned its Living Room, my favorite place to loll around a crackling fire, with a thimble of Lagavulin and an iPad. Along with  two adjacent bars, the Living Room buzzes and makes for some over-the-top people watching. Indulge on caviar and foie gras at its celebrated restaurant, Element 47, named after silver’s atomic number on the periodic scale; Matt Zubrod’s a great chef, and with exceptions, his menu is mostly built around local ingredients.

The Little Nell/Photo Courtesy of the Aspen Skiing Company

The Little Nell/Photo Courtesy of the Aspen Skiing Company

New this season: the Chef’s Dining Society, a gourmand experience for four to eight persons. Enjoy your own private chef and sommelier, along with five-courses and premium wines; your feast is held either in the cellar, with its award winning 20,000+ bottles overseen by Master Sommelier Carlton McCoy, or the dining room.  At $1,000 a person, it promises to be a memorable, though not exactly budget night. But hey, it's all about Living Well.

The Wine Cellar at The Little Nell/Photo courtesy of the Aspen Skiing Company

The Wine Cellar at The Little Nell/Photo courtesy of the Aspen Skiing Company

Earth-hued tones warm the understated luxury of the Nell’s rooms. Slink in to the sleek Holly Hunt custom-designed furniture, surrounded by contemporary art. Splurge on one of six signature suites; book the Paepcke, overlooking Aspen Mountain. The suites are so exclusive that you can’t reserve on line and must call a specialized concierge at 855-441-1516.  Luxury doesn’t stop with you; even Spot gets a custom bed and epicurean treats, private walkers, and amenities, like the Puppy Jet Lag kit. After all, with the town’s elevation of 7,945 feet, you’re not the only one who needs to acclimate. Before you know it there'll be doggie snow and après happenings. Yup: welcome to Aspen. And when it comes to your skis, even the Nell’s tuning is five star. 

The Hotel Jerome, Aspen’s first hotel, opened in 1889. Like many, I have a special place in my memories and my heart for this landmark, which received a gorgeous, loving renovation and luxe upgrade in 2012, and is now managed by one of my favorite brands, Auberge Resorts. Its 93 rooms offer lots of quirky features, like old-style steamer trunks. 

Photo courtesy of the Hotel Jerome

Photo courtesy of the Hotel Jerome

Want more of a hideaway from busy Aspen?  Check in to The Viceroy Snowmass, with ski-in/ski-out. I love sipping cocktails fireside in its stylish Lobby Bar. The rooms, which range from studios to four-bedrooms, are, however, less quirky than its Jean-Michel Gathy designed public spaces. Its chef Will Nolan is one of my local favorites; the flavors at its Eight K restaurant reflect the influence of his New Orleans’ roots. The spa, while limited, is serene, with treatments branded with motifs from the Ute Indians who once inhabited the area in summer. For pure indulgence, book its two hour treatments, the Bear Dance Ritual and the Sun Dance. 

Two other hotels that I really like, and often refer friends to, are the Limelight Hotel, with generous-sized rooms, and family friendly activities. And the Aspen Meadows Resort, the Bauhaus-inspired complex on the Aspen Institute's campus in the West End, just minutes from downtown by shuttle or car. The setting—so beautiful and peaceful—makes you feel worlds away from the busyness of Aspen.

Après SKI

Assume your position at Ajax Tavern at the base of the mountain, on the patio if weather permits, or jam into one of its cushy red leather booths inside. Your reward: amusing people watching, live music (outside), and an In-and-Out House-style double cheeseburger with truffle fries, or fondue. Downstairs, the Little Nell’s Chair 9 bar overflows with a mix of out of town hedge funders and locals.

The younger crowd heads across the street to the pool and hot tubs at 39 Degrees lounge at the Sky Hotel (scheduled to become a W hotel ). 

The J Bar at the Hotel Jerome still feels like an authentic saloon. Channel its Wild West and hippies' era history; Hunter S. Thompson and celebs like Jack Nicholson and Bill Murray misbehaved here frequently. Chug down an Aspen Crud—its signature drink from Prohibition days—a vanilla milkshake laced with bourbon. The Jerome’s renovated living room has become a local’s favorite for aprés and night caps.

Photo courtesy of the Hotel Jerome

Photo courtesy of the Hotel Jerome

Mellow out at the Limelight’s comfy living room with fireplace, while listening to live music and noshing on affordably priced hand-tossed,  thin-crust, delicious brick-oven pizzas. 



Victoria’s makes the best cappuccino and chai lattes in town, along with hearty breakie wraps,, and delicious gin-cured house gravlax with eggs. You’ll also love the local scene and eggs benedict at Peach’s Corner Cafe. Spring Cafe offers a vegetarian menu with lots of gluten-free and vegan dishes that even meat lovers will find delicious, like the huevos rancheros and, a favorite of mine, the tofu scramble. 


If I’m not on the mountain, you'll find me at White House Tavern. The fried grouper sandwich, the big cheeseburger (you can also wrap in lettuce leaves), and the stacked prime rib with French dip, all served on housemade bread, are my idea of delicious calories. Order the Thai noodles salad with steak, packed with flavor. They don’t take reservations, so get there either early or late, or expect to wait; or if you’re solo, snag a seat at the bar. 


While I sometimes sit down for a full meal, I tend to do a dining crawl, going from restaurant to restaurant, sitting at the bar and ordering small plates. 

The cozy French bistro Creperie du Village makes me feel as if I’m in the French Alps. The food is classic and delicious, from crepes to raclette and fondue.

At the cozy Ellina bar order its artichoke-heart bruschetta; pork belly tacos; and chicken milanese. You'll love the ambience.

There’s nothing in Aspen quite like the food at Chef's Club by FOOD & WINE at the St. Regis Aspen Resort. Overseen by longtime local chef Todd Slossberg, the restaurant spotlights dishes from Food & Wine magazine’s Best New Chefs, with special-event dinners featuring these culinary stars and other visiting chefs, throughout the year. The dining room is pretty, but I love sitting at the counter that looks onto the open kitchen, and seeing my meal being prepared. I also love sitting at its intimate bar, which offers some of the best artisanal cocktails in town. 

Since the day it opened, I’ve been eating at Matsuhisa, with Nobu’s sublime sushi gourmet Japanese dishes. Reservations are tough to get downstairs during the season, so try the first-come first-served upstairs. Most of the dishes are available upstairs, at a slightly lower price.  

The fashionable Cache Cache is an Aspen mainstay with a solid French-American menu, like classic roast chicken. Its wine list is packed with great Burgundies and Champagnes. I head for its no-res bar, which turns in to a scene later in the evening.  

Meat and Cheese offers a delicious farm to fork menu in an informal setting that’s also a store, and you can pop in for apres ski drinks and snacks too. I’m a David Chang fan, and there’s nothing as close to his flavors in Aspen as its Bossom Korean pork board,  with housemate kimchi, my favorite dish.

Meat & Cheese/Photo by Janet O'Grady

Meat & Cheese/Photo by Janet O'Grady

And I love Hooch, its sister speakeasy downstairs, for evening snacks and artisanal cocktails. 

Aspen is fortunate to still have Explore Booksellers, housed in an authentic Victorian on Main St. with a small but interesting selection of titles. Upstairs you’ll find one of my favorites places, Pyramid Bistro. Chef Martin Oswald creates yummy, healthy food from vegetarian dishes to sustainable fish and chicken dishes. The bookstore and the Pyramid are sanctuaries of calm, especially during Aspen’s busiest times of the year. Nightlife 

Your legs may be tired after a day on the slopes, but take a nap. The night amps up, and you don’t want to miss live music and dancing at Belly Up

There are a limited number of weekly memberships available to the Caribou Club—Aspen’s first private club; ask your concierge for help, or call Billy at 970-925-2929. I love chef Miles Angelo’s food, some of the best in town. After dinner, it’s all disco and party. 

Jazz Aspen Snowmass, which sponsors June and Labor Day festivals, presents intimate winter and summer performances at its JAS Café program. Held Downstairs at the Nell, and the Cooking School of Aspen, the music ranges from classic jazz to Latin and Cuban and blues. 

What to Pack:

Unless you already own a ski outfit you can’t live without, wait until you arrive in Aspen to buy one. When it comes to ski fashion, Aspen is cutting edge, especially at the two shops below. Also where you should buy ski boots and buy/rent skis. 

Want that cool Aspen Look that combines city and mountain functional style? Head to Performance Ski 614 East Durant for trend setting clothing, and top of the line skis. Check out its Authier label, from co-owner Lee Keating. Also on sale: the Aztec brand, inspired by Aspen, whose co-owner grew up here.

Gorsuch, at the base of Aspen Mountain, is an alpine institution, with top brands, from skiwear to streetwear.

Ute Mountaineer sells a great selection of the top brands for backcountry ski gear and apparel; you can also rent cross country and telemark skis and boots too. The staff at this locally owned shop is knowledgable too.


Aspen’s blessed with mostly Rocky Mountain super sunshine, even on cold days. Which makes me want to get outdoors as much as I can, and, with the right layers and footwear, you'll want to too. There are many ways to get out of your comfort zone like exercising outside—and it sure beats the gym. 

Photo courtesy of the Aspen Skiing Company

Photo courtesy of the Aspen Skiing Company

For years I had a fox terrier, and for years I walked her up Smuggler Mountain, even in winter. Though my doggie is no longer with me, I still prefer a walk up Smuggler in the brisk air over a spin at the gym. At certain hours the trail can be crowded, but go beyond its first platform, where most people stop and turn around, and you’ll have most of the trail to yourself. You can even “borrow" a dog from the Aspen Animal Shelter.

Skin Up a Ski Mountain to experience nature as well as to physically push yourself. You need alpine touring skis, bindings, and boots that give you the mobility to move up the hill,  but provide stability when you descend. Poles are longer to provide more support on the ascent. For the climb, skins—heavy-duty nylon that adheres to the base of your skis to keep you from sliding while going uphill—are then removed for the descent. Ute Mountaineer

Aspen Cross Country Center is located at Aspen’s municipal golf course, with many groomed beginners' trails. It’s a great work out, and hey, you’re outside. Trails are free, you can rent skis there, and do take lessons. 

I love the knockout views up the Castle Creek Valley, and the Nordic Ashcroft Ski Touring located near the ghost town of Ashcroft. Here you’ll find some 22 miles of trails for X-C skiing—which I prefer over snowshoeing. Then linger over lunch at Pine Creek Cookhouse. In the evening dinner is served, and you can access it either on skis or a romantic sleigh ride.  

The backcountry is a powerful digital detox. The non-profit  10th Mountain Division Huts, named after a division of soldiers in the US Army who trained in Colorado, oversees 34 huts considered the best in Colorado. Book early as the huts fill up quickly, especially for full moons. This is serious wilderness skiing, so it’s important to hire a guide knowledgable about avalanches—a frequent danger— and routes. You must strap on an avalanche beacon and shoulder a pack with provisions. Then enjoy the beauty as you glide, climb, and slide. The wooden huts are basic but cosy, with some solar and wood burning stoves. Closest to Aspen is the McNamara. 

What Locals Should Tell You

Traffic in Aspen gets gridlocked during peak times, including to and from the slopes, and downtown parking is expensive and hard to get.  So do not rent a car, as excellent public transportation exists. Taxis are available but expensive, and during peak times, you can get Uber. The major hotels all offer private car and shuttle services.

Aspen's a friendly town, so get to know the locals, including your bartenders, who will tell you the latest gossip, as well as last minute news on openings and events around town. 

More A List


Jimmy’s Bodega





Aspen Art Museum

Baldwin Gallery

Anderson Ranch Arts Center

Aspen Film Festival