Charles Cunniffe has made his mark on Aspen—and vice versa. A resident of the mountain town since the late-1970’s, the noted architect chose Aspen as the home of his namesake architecture, planning and design firm, Charles Cunniffe Architects, which has become known for its luxury-meets-sustainability ethos. Among the studio’s projects are upscale golf courses, private ski estates (a favorite of tech moguls and celebrities), community housing, a stunning new firehouse in Snowmass Village and the remodels of Aspen’s Wheeler Opera House and historic St. Mary Catholic Church.
Cunniffe is also as passionate about living in Aspen as he is in making it more beautiful. We asked him for his top five picks for what to do in town this winter—in between the skiing and the apres, of course.
Step into Infinity
Japanese artist Yayoi Kusama has been creating versions of her signature mirrored infinity rooms since the 1960’s, but the immersive installations are enjoying a resurgence in worldwide popularity in this age of technology and social media. While you’ll find long lines outside the Kusama exhibits in cities like New York and Paris, visiting the newly-installed Where the Lights in My Heart Go at the Aspen Art Museum is much more manageable—and just as moving. “We are so fortunate to live in a ski town with world-class art like this Kusama’s Infinity Mirror Room, where there are less than two dozen of these installations around the world,” notes Cunniffe. “The 10×10’ immersive kaleidoscope is like nothing I’ve experienced.” Another Cunniffe tip: go when Museum opens at 10am, then stay for lunch at the rooftop restaurant.
Buy Out a Cloud
Located at the Aspen Highlands, at the top of the ski lift, the legendary ski-in, ski-out Cloud Nine Bistro is a favorite for its cozy ambiance, European Alpine-inspired fare, and lively apres scene. This year, for the first time, the place can also be all yours for an unforgettable dinner. “Cloud Nine has always been a favorite of locals and tourists alike, known for flowing champagne, fondue and lively dance parties,” says Cunniffe. “But my favorite way to enjoy it is by booking an intimate dinner with friends, and riding the open-air snowcats to and from the bistro, which is set at 11,000 feet.” Food and beverage minimums apply for the evening buy-outs, which are available until April. “Don’t miss the Colorado Wagyu Beef and the Truffle Tagliatelle,” recommends Cunniffe.
Have Half of Aspen Mountain to Yourself
In addition to offering its guests stellar service, plush accommodations, and some of the best food and wine in town, The Little Nell hotel also grants them private access to Aspen Mountain’s backcountry with its Snowcat Powder Tour. Offered on Wednesdays and Fridays, for up to 12 guests (at a cost of $625 per person), the experience includes the chance to ski 10-to-12 untracked intermediate-to-expert runs, followed by a gourmet lunch with sommelier-picked wines, and chair massages from a spa therapist. “Skiing Aspen’s backside this way is pure magic, with the untracked champagne powder, remarkable scenery, and wonderful cabin lunch,” enthuses Cunniffe. For the best experience, he suggests “watching the storm cycles in Northern California, and when they are dumping snow in Tahoe, book your powder tour for three-to-four days later.” Note that the adventure is available exclusively to guests of The Little Nell, Residences at The Little Nell and The Limelight Hotels.
Go Where Aspen Meets the Amalfi Coast
With its setting on the Amalfi Coast, in the foodie favorite village of Nerano, the iconic Conca del Sogno restaurant is known for is fresh sea-to-table fare. After the success of transporting those flavors to New York City during a Chefs Club residency, the Conca team has now headed to Aspen, where they will take over the Chefs Club inside the St. Regis Aspen resort for the winter 2019-2020 season. “Having the pleasure to dine at one of Italy’s great restaurants right here in Aspen is such a treat,” says Cunniffe. “If you can, book the fireside table—it’s spectacular. And don’t miss the whole branzino, served tableside, and the pistachio profiteroles.”
Catch Fireworks from a New Rooftop Lounge
Originally started in 1951 as a way for locals to toast to winter and the town’s Nordic lifestyle, Aspen’s annual Wintersköl festival has grown to feature four days of festivities, from ice sculpting contests and canine fashion shows to soup-making contests and full moon dinners. It all gets capped off with fireworks, which this year Cunniffe recommends enjoying from the rooftop of the new W hotel. “I’ve been lucky to be able to celebrate Wintersköl for 40 of its 69 years, and this year, am excited to head to this new rooftop to watch the evening torchlights descend Aspen Mountain and end in fireworks,” he says. “The downtown ice sculptures, the canine parade, the celebrations on all four mountains—it’s one of my favorite weekends.”