The slopes and heated sidewalks (yes, really) in Aspen, Colorado are always abuzz during ski season but this decadent municipality is more than just a bougie playground for ski bunnies. “Many people think Aspen is a winter destination, but personally, I think it comes alive in the summer,” says Carol Hooper, head concierge at The Little Nell, a five-star property situated at the base of Aspen Mountain.
Anna Hansen-Armstrong, a yoga teacher and Colorado native who calls Aspen home, concurs: “It rarely gets above 90 degrees and if it does you can just jump in the river and cool off,” she says. Enjoy hiking, biking, rafting, fishing, and paddle boarding during the warmer months, and stay on through fall for incredible leaf peeping.
A calendar full of events also keeps people flocking to Aspen, as Lloyd Christmas describes in Dumb and Dumber, like the “salmon of Capistrano.” Rub elbows with Olympians during the X Games (January) and the Audi FIS Ski World Cup (March), or dine alongside culinary connoisseurs from around the globe at the Food and Wine Classic (June). Come Labor Day weekend 2023, catch the Foo Fighters, The Lumineers, and Old Dominion headlining at Jazz Aspen Snowmass.
In short, there’s never a bad time to touch down in this luxurious locale that offers all the creature comforts of a “metropolitan city in four square blocks,” says Jamie Contractor, bar and events director at Kemo Sabe, a famed boutique known for its upscale Western wear. Here, six Aspen insiders explain how to leave this magical mountain town with your heart full and your wallet empty, no matter the season.
Check Out Aspen From Above
Ascend Aspen Mountain aboard the Silver Queen Gondola, which whisks you up 11,200 feet. Enjoy the view from the patio at Sundeck restaurant or channel your inner Von Trapp child by frolicking through the fields of wildflowers that blanket the Rockies in spring and summer. On Sundays, the hills truly come alive with music when Colorado’s top bluegrass bands assemble at the peak to play for locals and tourists alike. Yogis can also stretch out and perfect their mountain pose in a majestic setting Monday through Friday when the Aspen Shakti team teaches an hour of open-air Hatha yoga starting at 10:30 a.m.
Hit The Trails
A gondola isn’t the only way to get around in Aspen but to swiftly scale the Rockies you will need a four-wheel drive car. Audi’s new Activesphere Concept vehicle is specifically designed to transport you (and all your gear!) up and down the mountain. This fully electric crossover coupe with 22-inch wheels transforms into a pickup truck—making it roomy enough to haul everything from skis to e-bikes. This self-driving automobile also comes equipped with a high-tech accessory: augmented reality goggles that seamlessly merge the physical and virtual worlds. While this futuristic car isn’t available just yet, Emilie Cotter, chief communications officer at Audi of America, says guests of The Little Nell can take the Audi e-tron SUV for a complimentary, two-hour spin to check out the scenery.
Those who really want to get off the beaten path can explore Aspen’s wilderness on foot. “Within the valley, you’ll find everything from beginner to advanced trails — you can even climb fourteeners [mountains that are 14,000 feet or higher], which I like to do,” says Contractor. Two picturesque paths worth taking: American Lake and Lost Man Trails. “Another popular option is to hike between Aspen and Crested Butte, which is about 11 miles,” says Hansen-Armstrong. “You can stay at the Eleven Scarp Ridge Lodge or have someone pick you up at the trailhead.”
Go For A Spin
Hop on a bike and explore one of the area’s many trail systems. Hansen-Armstrong, an avid cyclist who also happens to be married to seven-time Tour de France champion Lance Armstrong, says Tom Blake Trail and Sky Mountain Park are two of her favorite places to mountain bike whether you’re a beginner or a bona fide pro. Road riders can bike up to the Maroon Bells (two of the most photographed mountain peaks in North America) or take the 42-mile Rio Grande Trail that stretches from Aspen to Glenwood. “If you don’t think you can make it all the way [solely by pedaling], rent an electric bike,” advises Hansen-Armstrong. Reward yourself after a long ride at Woody Creek Tavern (a local watering hole) or enjoy the stunning views at Pine Creek Cookhouse (which can be reached in the winter by cross-country skiing, snowshoeing, or hopping aboard a horse-drawn sleigh).
Find Time To Unwind
After an active day outdoors, Hooper recommends soothing tired muscles and adjusting to the altitude at the only five-star spa in town, which is tucked inside The St. Regis Aspen Resort. Before or after a decadent massage, facial, or body scrub, enjoy the oxygen lounge, cold plunge, and co-ed waterfall pool. Sweat out any stress during hot yoga at 02 Aspen or find your flow at Aspen Shakti—two of the studios where Hansen-Armstrong teaches. Both fitness spots also feature in-house spas where you can book everything from a spray tan (02) to an astrology reading (Aspen Shakti) post-class. If your feet need some TLC after being jammed into hiking boots, head to A1 Foot Massage, a no-frills establishment locals love, says Contractor.
Please Your Palate
Downtown Aspen packs a serious culinary punch—especially if you’ve got money to blow on caviar and kobe beef, which are almost always on the menu. “There is a group of really passionate chefs that incorporate the alpine spirit into their cuisine,” says Kyle and Katina Connaughton, the chef-farmer couple behind SingleThread Farm, Restaurant, and Inn in Healdsburg, California. The culinary duo and Aspen regulars suggest starting your day with a coffee at Felix Roasting Co. or a full breakfast at Bear Den. Swing by Spring Cafe for lunch and stop at JUS for a fresh-pressed juice, says Hansen-Armstrong.
If you’re looking to indulge at dinnertime, make a reservation at Bosq (a “must” according to the Connaughtons) or Steakhouse 316, which Hooper deems the “epitome of historic Aspen.” Newcomer Madame Ushi Aspen serves up Asian fusion in a swanky space covered in hand-painted murals. Don’t miss the tuna flight, Hooper’s favorite dish. Sushi and cocktail lovers will also enjoy Matsuhisa, chef Nobu Matsuhisa’s namesake restaurant. Order The Gardener, a verdant drink made with tequila that Hansen-Armstrong and her friends like to call their “green juice.” Or, do sake bombs with Frank Lu, executive chef and owner of Jing. “He’s a local celeb!” says Contractor. Other reservations worth making: Ellina, Chica, Acquolina, Casa Tua, Cache Cache, Clark’s, Mi Chola, and Las Montañas.
Stay Out Past Your Bedtime
After supper, scoot your boots over to Hooch, a subterranean cocktail bar with a speakeasy feel, says Contractor. Or, dine at Campo de Fiori, an Italian restaurant run by general manager David Ellsweig (known to locals as “Campo Dave”). “The bar becomes kind of wild late at night!” notes Hansen-Armstrong. A string of nightclubs—including Gala, The Sterling, and Ponyboy—are perfect if you want to heat things up on the dance floor and Belly Up is the best venue for catching a concert. “It’s the greatest place to see a show because there’s not a bad seat in the house,” adds Hansen-Armstrong.
Leave Room For Souvenirs
“Aspen has all the charm of a sleepy ski town with boutiques from some of the best brands in the world,” says Cotter, who made time to window-shop while in town for the Audi FIS Ski World Cup. Designer gear from Gucci, Dior, and Ralph Lauren is abundant if you need a luxe lodge look or a pair of Prada bike shorts. There are also plenty of local gems, including Max (which features a carefully curated selection of clothing and accessories from brands like The Row and Celine); Pitkin County Dry Goods (a boutique featuring an eclectic mix of designer and contemporary labels); and Carl’s Pharmacy (a one-stop shop for everything from wine to wrapping paper). Treasure hunters should visit Susie’s and The Little Bird for “not-to-be-missed consignment,” says Hooper.
The one thing you really can’t leave town without is haute headgear from Nick Fouquet or Kemo Sabe. The popularity of these iconic Aspen stores is evidenced by the number of people sporting cowboy hats in the streets (and the plane ride home). Outside of Kemo Sabe’s legendary hats that can be branded with your initials, Contractor recommends buying a pair of the store’s customizable Grit boots that are perfect for parading around Aspen in any season.
Gear Up For Ski Season
It’s never too early to start planning a winter escape to experience the “best powder in the world,” says Aleksander Aamodt Kilde, a Norwegian alpine skier who recently secured his second consecutive Crystal Globe at the Audi FIS Ski World Cup. The pro recommends taking advantage of all four mountains—Aspen Mountain, Buttermilk, Aspen Highlands, and Snowmass—each of which boasts its own unique landscape and set of challenges. Another option: Explore the equally impressive backcountry via snowcat (a fully enclosed, all-terrain vehicle), says Kyle Connaughton. For the best view of the Maroon Bells, book a snowmobiling excursion through T-Lazy-7 Ranch or take a guided snowshoe tour of Aspen Mountain or Snowmass with the Aspen Center of Environmental Studie, adds Hooper.
Après All Day
You don’t necessarily need to ski to join the town-wide soirée that kicks off when the lifts stop turning. “If you're a hardcore skier, you're probably at the base of Highlands getting a beer in your ski clothes,” says Hansen-Armstrong. “There’s also a different kind of après where people wear makeup and have washed hair!” One spot that does require you to brave the slopes is Cloud Nine, which delivers a daily champagne shower at 2 p.m. Expect to find the crowd “dancing in their sports bras and ski pants” while being sprayed with Veuve Clicquot, says Hansen-Armstrong. If you’re seeking booze-fueled debauchery that doesn’t require a raincoat, consider The Snow Lodge (which features an outdoor concert series and DJs in The Blue Room) or enjoy the views from the Aspen Art Museum’s rooftop party on Saturdays.
For a slightly chiller scene, find a seat at Ajax Tavern where you can watch skiers make their final runs and order truffle fries, says Contractor. Head to Hotel Jerome for fireside cocktails, order a beer and a burger at J-Bar, or sip an Instagram-worthy hot chocolate at The Little Nell. If you want to host your own après gathering like the Connaughtons, pick up provisions from the farm shop at Meat and Cheese, wine from Of Grape and Grain, and a bottle of bubbly that can be savored instead of splashed across an Alpine bistro.
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