It’s rare for dedicated skiers and snowboarders to find bucket list runs on resort slopes, but Aspen is home to more than a few surprises, and not just the expected celebrity sightings. The four local mountains in the Aspen Snowmass family are teeming with graduated slopes and sweeping chutes. The smallest of the bunch, Buttermilk, is prime beginner and intermediate terrain, but has also become something of an icon to park and pipe enthusiasts as the home of the Winter X Games for 14 consecutive years. Neighbouring peak Snowmass is teeming with terrain—94 trails and 1,343 meters of vertical to be exact. The mountain, like its siblings, is littered with shrines to celebrities and musicians such as Frank Sinatra and author Hunter S. Thompson; none of them marked on maps, each a unique takeaway for skiers looking for a new angle to explore while dipping through glades. Aspen Mountain is the city’s pioneer peak, established in 1947, and is home to the bulk of the shrines, including nods to Jerry Garcia, Jimi Hendrix, Elvis, Marilyn Monroe, and more. Better known as Ajax, the hill rises right from the downtown core, its easy access making it a favourite hill among locals, many of whom simply zip over for a few quick turns over their lunch hours or meet for a bite at the Sundeck, where the view is simply spectacular. There is perhaps, though, no view to be beaten on a bluebird day than the one from the top of the Highland Bowl.
Situated behind Aspen Highlands mountain’s main face, off Deep Temerity, the Highland Bowl is the holy grail of in-bounds skiing. Skiers line up at the ridge to hitch a free ride on a Snowcat that will drop them at the base of the hiking trail. From there, it’s about a 30 to 45-minute trek to the top (depending on fitness and how acclimatized one is to the altitude). Although the size of the route can make you feel like you’re in the backcountry on a windy day, the ridge is plenty safe, boot-packed and avalanche controlled by ski patrol each viable morning to eliminate the threat of avalanches. At 12,392 feet above sea level, Nepalese-style prayer flags are a cheerful indicator of the summit, and a small lift chair is anchored for photo ops—doing a bowl run ensures serious bragging rights, and photo evidence is a necessity. The beauty of skiing the bowl is finding those bits of untracked snow through one of the chutes, and lining up early to catch the cat for a first run can reap some serious rewards. Whichever route you choose (there are nearly 20 options), they all funnel back to the Deep Temerity chair.
“If you hike the bowl, you’ve definitely earned a trip to Cloud Nine,” declares Lea Tucker, international public relations, senior manager for Aspen Snowmass. Reservations are a necessity at the small mid-mountain fondue restaurant, where generally there are two seatings, the latter of which cements Aspen’s reputation as a party city and sets the bar for all other après to follow. The food is good, yes, and first timers may note that almost every diner has paired their meal with a bottle or two of Veuve Clicquot. The volume of the music steadily rises—“Pour Some Sugar On Me”, naturally, followed by “I Love It” by Icona Pop featuring Charlie XCX—and patrons begin to dance on chairs and benches. Without warning, someone is spraying champagne, inciting a room wide spray-off, a Cloud Nine Alpine Bistro tradition that has made the establishment the largest purveyor of Veuve Clicquot in the state. The dance party wraps after about 10 tracks, and staff clear out partiers around last chair.
In town, Hotel Jerome is home base. If heaven were a decked out ski lodge, it would take cues from this grand dame of Aspen. The lobby is lined with elegant furnishings, all complimented by eclectic Americana design touches—oil paintings, vases and china, antlers—that exude sophistication and comfort. The AAA Four Diamond award-winning hotel spares no detail in any of its 94 well-appointed suites, either. LCD televisions and iPads are standard in every room, as are soaker tubs, separate walk-in showers, and plush robes. A private deck for guests on the top floor offers stunning views of the city, particularly at dusk when twinkling streetlights chime in and the face of Aspen Mountain is still lit. The hotel is also home to classic American dining at Prospect Restaurant, prohibition-style libations at the Living Room lounge, and all matters of après at the famous J-Bar watering hole, where the drink of choice is a boozy milkshake known as the Aspen Crud.
In town, an assortment of restaurants and lounges play host to a diverse après crawl: beer flights at local Aspen Brewery, burgers and Parmesan truffle fries at Ajax Tavern, sushi and sake at Matsuhisa, and live music at BellyUp (host to acts including the Flaming Lips and G. Love and Special Sauce). Jimmy’s Bodega is the new kid in town, delivering fresh seafood and raw bar items paired with specialty cocktails. The ultimate in exclusive post-slope surrender, however, is an elite membership to the Caribou Club. An Aspen institution for 24 years, membership prices are steep and exclusivity is prized; staff famously turned away an A-list actress looking to gain entry for the evening. Once in, lounging in the Great Room by the fire while exploring the extensive wine list and people watching is highly recommended.
In the light of day the mountain town does play host to some of the expected sights, European tourists with collagen-plumped lips wearing exorbitant amounts of fur; they wander the brick-lined mall, Burberry and Ermenegildo Zegna bags in hand, but Aspen’s unexpected richness arrives via culture and taste. Stopping in the Aspen Art Museum and grabbing a fresh farmhouse-style lunch from Meat and Cheese are great sendoffs before departing to Telluride, a four-hour drive south and west.
Along the highway there are few stops. Mountain passes are lined with craggy cliffs that show flesh tones of red, orange, and purple through drifts of snow. In Telluride, the frontier roots of the Midwest start to show through, and on an historic walking tour with local guide Ashley Boling, remnants of the town’s cowboy, mining, and saloon days remain. An unassuming white door on East Colorado Avenue holds a plaque alerting passersby to a unique historic event on June 24, 1889. “This is the site of Butch Cassidy’s first-ever bank robbery,” announces Boling, personifying Telluride’s quiet pride. The mountain speaks for itself.
A gondola connects the town of Telluride to Mountain Village. No less than six dining experiences are noted on the Telluride trail map, with some stellar standouts: Alpino Vino is North America’s highest restaurant, but the views are merely an amuse bouche. Located at the top of See Forever trail just below Lift 14, the on-mountain spot serves Italian bites, and, as its name suggests, a selection of wine. Settling in on a daybed and choosing a bottle from the outdoor wine bar is a must for lunch on bluebird days. At dinner, wine continues to flow from the Allred’s award-winning wine list, best paired with sustainably-sourced elk, lamb, or steak.
The trails of Telluride offer something for everyone, and draw many an outdoor enthusiast far from home. A variety of backcountry trails for eager freestyle skiers are accessible from lifts, and beginner, intermediate, and advanced skiers can find common ground in the myriad runs off of Prospect Express. A quick recognition of like minds arises after spending time in Colorado—perpetual grins are plastered to the faces of visitors and locals alike, on and off the slopes, and it’s not hard to understand why. Surrounded by the majesty of the San Juan and Elk mountain ranges, there is a calling heard by those who seek the peak, quieted only by the soft downfall of snow.