Aspen: A Local’s Winter Guide

Aspen offers visitors a combination of small town Western charm with the allure of high-end hotels, delicious restaurants and big city shopping. Attracting everyone from die-hard skiers and snowboarders to families, celebrities and the international jet set: Aspen truly caters to all. We recently got back from a long weekend skiing with friends who call Aspen home, and grilled them to share all their favorite spots with Daytripper365.  Here’s Stacey’s ideal day, combining her husband and friends favorites into the ultimate Rocky Mountain winter playground guide.

Tripper Tips:

During the winter months fly into Eagle airport in Vail, as Aspen airport often shuts down in bad weather. From Vail it’s approximately an hour and a half drive. You can rent a car or organize a taxi.

Aspen gets crowded during the season— reserve lift tickets, restaurants and spa services in advance.  Purchasing your ski passes online from home will save you money.

Shipping equipment and outerwear makes life, and travel, easier and should be done at least one week in advance. Fedex ground insures prompt delivery within 5-7 days.

Ski: You won’t get bored of the terrain at Aspen with four different mountains to choose from. Aspen (commonly referred to as Ajax) is right in town, with Buttermilk, Highlands and Snowmass, a short drive away. Lift passes are interchangeable and there are free shuttle buses from town to the various mountains. Novices beware: Ajax has no beginner runs! For groomers and wide-open trails head to Buttermilk or Snowmass. (Serious skiers/boarders will still find plenty of challenging terrain at Snowmass.) If you’re looking for an uphill challenge, hike to the peak of Highland Bowl.

Stay: For ski in, ski out, you can’t beat the Little Nell right at the base of Ajax Mountain. With great service, a cozy atmosphere and prime restaurants for après ski and dinner you don’t have to go far. They provide free shuttle service—around town and between the ski mountains—a big plus! I’ve also sent friends to the St. Regis, Hotel Jerome and the Sky Hotel when the Nell is full. Got little tykes? Snowmass is the best mountain for kids, stay slope side at the family friendly Viceroy and get to ski school in seconds. 

Coffee: Rushing to ski Ajax and just want to grab a quick espresso? I like Ink, right across the street from the lifts. Just down the block, Victoria’s Espresso baked goods pastries are made fresh every day, try the morning glory muffin. 

Best Breakfast: Sure the lines are long at ever-popular Poppycocks and friends swoon for their blueberry oatmeal pancakes. Over Easy does a nice breakfast and if you hit the slopes early, Bonnie’s on the mountain serves pancakes till 10:30. My favorite is Jour de Fete for great egg sandwiches—my favorite is the scramble with spinach on a croissant.

Yoga: I like Shakti Shala right in downtown, but I go as often as I can to Aaron’s class at King Yoga, just a ten-minute drive out of town. (Located across from the airport in the ABC complex.) The vinyasa flow class is a mix of Aaron’s own sequencing—to a backdrop of excellent music. (He used to work in the music business) You’ll be on a high all day after this class!

Hide and Seek: You could look all day and still not find many of Aspen’s hidden shrines; created by locals and hidden in the trees just off the trails of Ajax and Snowmass. Some are elaborate, while others are just a single plaque. One of the most popular is a tribute to singer Jerry Garcia (Off Ruthie’s Run on Ajax) complete with red roses, drawings, a bench, photos, and a signed guitar! For more detailed information on the shrines click here. 

Lunch: At the bottom of the gondola, Ajax Tavern is everyone’s go to—you deserve the burger and fries after skiing all morning. Stay on the mountain and ski to Bonnie’s. In town, Meat and Cheese is one of my favorites for great salads, sandwiches, plus their signature meat and cheese boards. Don’t skip the excellent thai coconut soup. (You can stock up on gourmet provisions here as well.) I get cravings for the macho salad at White House Tavern--you will too! One of my hidden gems is Pyramid Bistro, a small cafe on the second floor of Explore Booksellers. (It’s a great independent bookstore, allow time to browse.) Here it’s all about healthy cuisine—with options for vegetarians and their meat-eating companions.

Rocking Lunch: Looking for a party? Spend a day skiing Highlands and channel St. Barth’s with lunch at Cloud Nine at the top of Highlands. It gets rocking as the day goes on--so fun--especially with a group!

Apres Ski: There is no better feeling than loosening your boots at the end of the day while sipping a cocktail and perhaps some Parmesan fries at Chair 9 at the Little Nell. (The lobby lounge is dog friendly if you have any furry friends with you!) Across the street, it gets lively at 39 Degrees in the Kimpton’s Sky Hotel. I have spent many ‘happy hours’ with friends at the bar at the Jerome Hotel, an Aspen classic with an Old West atmosphere.

Shopping: My favorite store hands down is Performance Ski, not only for amazing ski clothes but also for other fashion finds from owner Lee Keating. For the softest exercise and yoga gear--stylish enough to keep on all afternoon—I love SQN Sport. For extravagant purchases, I stop by Max and Nuages, both boutiques sell high-end designer clothes, both are extremely well curated. Pitkin Country Dry Goods is a go to for more casual clothes and accessories. Other good ski shops are Stefan Kaelin Ski and Golf, Miller Sports, or Gorsuch. Kemo Sabe is a great place for western gear without the kitsch. 

Pamper: Skiing can be hard work. Get rid of the kinks with a treatment at the ultra luxurious Remede Spa at the St. Regis. The Oxygen Lounge is especially good for altitude sickness, jet lag and hangovers! Another option is Aspen Alps Fitness--ask for Rosey, she’s amazing!

Smoke: With the legalization of recreational marijuana in Colorado, Aspen now has its share of dispensaries. If you’re over 21, you can buy weed in many varieties:  edibles (lollipops, mints, chocolates, baked goods.) infused drinks, vaporizers and even topical sprays.  Knowledgeable “bud tenders” are available to consult and help you with your purchases. My favorite shop's, Silverpeak, slogan says it all-- “socially responsible, from seed to sensation.” Other good dispensaries include Leaf, Stash and Green Dragon.

Pre Dinner Drinks: Located in a former bank, Justice Snow's has an incredible cocktail list. You might not make it to dinner.

Dinner: By far the best pastas in town can be found at casual Acquolina. The Italian food is delicious at Casa Tua, but here it’s also about the vibe. The upstairs lounge is a super stylish, cozy spot to spend the night. Upscale dining favorites include Cache Cache, Pinons and Element 47 at the Little Nell. (Ask Clayton, the sommelier, to show you their underground wonder of a wine cellar, which you can book for special dinners.) Steakhouse No.316 is the place if you’re in the mood for a steak. Kenichi is good for a casual, quick sushi fix, but I prefer Matsuhisa. Yes it’s pricey, but I’m a sucker for Nobu’s consistently excellent sushi, rock shrimp in ponzu sauce and yellowtail with jalapeno. Nice for couples, The Wild Fig, with mostly tables for two, is a small sleeper. We often go and share the whole fish. Food and Wine magazine’s Chef’s Club, at the St. Regis, features  a menu designed with signature dishes of award winning chefs from all around the country.


Late Night Bites: Jimmy's has great food, killer drinks and is open late! 

Late Night Music: If you have any energy left to dance after skiing all day, head to Bootsy Bellows, a new basement lounge bar following in its LA sister’s footprints. I’ve seen some big names at Belly Up, a live music venue and bar, check ahead and get tickets as its small and often sells out. 


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