The road to untracked powder is paved with cold, sweaty discomfort. Or so I have convinced myself as I labor up a wintry mountainside, methodically placing one ski in front of the other for the umpteenth time while asking myself why I thought this was such a grand idea.

At least I’ve got company. On a late-April Saturday, professional extreme skier and mountain guide Chris Davenport is leading me up Quandary Peak near Breckenridge, Colo., the highest summit — at 14, 265 feet — in the Tenmile Range. We’re dressed to ski but first we’ve got to get to the top, an endeavor we’re undertaking one step at a time.

“Too bad about the weather,” Davenport tells me as we slog through an intermittent snowstorm, visibility near nil. “The views up here are killer on a clear day.”

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He would know: Davenport is the first person to have climbed and skied all 54 of Colorado’s 14,000-foot peaks within a year, a feat he completed in January 2007. He also won the World Extreme Skiing Championships twice (1996 and 2000), summited and skied Mount Everest, has appeared in some 30 ski movies, guides annual trips in Antarctica and looks nearly as comfortable in extreme, high-altitude environments as the wildlife that lives there.

I met Davenport through a mutual acquaintance, and he agreed to take me on an adventure. Dav, as he’s known to friends, chose Quandary because it’s one of the least technical 14ers to ascend, a nice feature when you can’t see beyond 20 feet. Sure, it’s a hulking chunk of planet — the next highest Tenmile peak is 13,951-foot Fletcher Mountain — but the standard summit approach on Quandary follows a well-protected route and, barring a colossal miscalculation, we can easily avoid the cliffs, chutes and avalanche-prone terrain that make high-Alpine skiing so dangerous. Our biggest challenge today is visibility, and Davenport warned me during our 2½ -drive from Aspen, Colo., where he lives, that the weather might force us to turn back before the summit.

At 9 a.m. he parks his black Chevy Suburban at a Forest Service gate just shy of the trailhead at 11,000 feet. As we sort gear and fill our packs, I’m anxious. I’ve done a few backcountry tours, but none this ambitious. Am I dressed in the right layers? Will my feet hurt or my hands freeze or — let’s be honest; this is my main concern — given a shot to ski with a pro, will I flail? I’m a fit, solid skier but also a 50-year-old Mid-Atlantic urban dweller. I can’t expect to roll into the Rockies cold and whistle up a 14er.

On skis rigged for uphill travel (with convertible bindings and climbing skins, strips of fabric stuck to the bottom of each ski, with thousands of tiny hairs that prevent backsliding) we start up on a trail through a forest of pine and spruce. It’s quiet in here, save for the occasional creak of a wind-bowed tree, and I’m reminded of why I so love backcountry skiing: meeting mountains on their terms, without the crowds, noise and infrastructure that resorts impose on the environment.

Davenport sets a brisk pace, skis and poles flowing efficiently forward, extensions of his limbs. At a lithe 5-foot-11 and 175 pounds, he’s not an imposing figure but projects command of his craft along with an infectious enthusiasm. If this is boring for him — an easy 14er, on a bleak day, with a flatlander — he’s hiding it well. I think he’s fired up to be outdoors, although it’s also clear he has expectations of me. He quickly puts 50 feet between us.

Davenport won’t take just anybody on an adventure. He needs to know you can ski up and down and that you won’t conk out — or freak out — way on up some mountain. (He had tested me the day prior with a 3,200-vertical-foot assault on Aspen Mountain, which I slogged through on five hours of sleep following a 1:30 a.m. arrival in town.)

After 45 minutes, we leave the trees behind and start up the long shoulder of Quandary’s east ridge. We climb steadily through a ghostly bubble of weather, which thins fleetingly to reveal the auburn shoulders of ridges looming in the distance, like whales lolling through the mist.

I’m feeling strong, especially when we pass two guys — one in a bright orange beanie and a circa 1977 parka — who had materialized out of the fog halfway up the ridge. They pepper us with questions on the route, the timing and the weather.

“Those two didn’t exactly look like they knew what they were doing,” Davenport says when we’re out of earshot. At 46, he still demands a lot of himself, with a summer training regimen that includes hiking up Aspen Mountain with a full five-gallon water cooler in his backpack. He spends hours on his road and mountain bikes — the notion to ski all the 14ers came to him during a 2005 bike ride — and, in winter, does a lot of what we’re doing right now.

“I spent 20 years in gyms,” he says. “I’m at a point where I just want to get my exercise outdoors.”

Wanna take the family on a ski weekend? You don’t have to break the bank.

He is also constantly pushing boundaries, a necessity in a niche that favors youth and audacity. Just before our trip, Davenport had done an extended ski-and-camp trip in Alaska’s Kichatna Mountains — “some of the steepest lines I’ve skied,” he says — and before that he had been in Bhutan, zipping around in a client’s jet trying in vain to get the government to allow first descents of some of the kingdom’s 20,000-foot peaks.

At 13,300 feet, my fitness evaporates. Suddenly I’m winded, wobbly and parched. The hill is steepening, my hands are cold, my thoughts murky and I feel outmatched by this environment. On the plus side, there’s a foot of soft, fresh snow underfoot, and I know we’re close to the top. Davenport is setting a tight zigzag skin track up the left side of a wide gully — eight steps one way, turn, eight steps the other way. The snow intensifies, whipping around us and chilling the sweat against my skin. I lock my gaze a few feet in front of my skis and will my legs forward.

Davenport started skiing competitively at 8 near North Conway, N.H., where he grew up. After graduating from the University of Colorado at Boulder (my alma mater) he took his passion to new heights by winning the US Extreme Skiing Championships in Crested Butte in 1994. “I fell in love with that competition format and realized I was really good,” he tells me, and that after his 1996 world championship win in Valdez, Alaska, “I thought, ‘I can make a life of this.’ So I wrote a business plan on the flight home.”

Davenport knew he could draw sponsors, but also knew that to build a business he needed more than free gear and plane tickets. “I approached these companies and said, ‘Here’s what I can do for you, and here’s what I want in return,’ ” he says. “A big part of it, frankly, was just being presentable” — that is, a contrast to the hard-partying stereotype of many young snow sports athletes.

He parlayed his accomplishments, which also include a 2014 induction into the U.S. Ski and Snowboard Hall of Fame, into commentator gigs on ABC, ESPN and Outside TV. He is part owner of the ski maker Kästle and his small army of sponsors includes Red Bull, Spyder, Aspen Snowmass and Scarpa boots. He’s also pitching a television show about chasing powder and has other projects in various stages of development.

“I see myself doing this for a long time,” he tells me, “and becoming an ambassador for the sport, like Billy Kidd and Stein Eriksen,” two former Alpine racers who enjoyed extended careers as poster men for the sport.

Toiling up the gully, I envision myself five hours in the future, eating pizza and drinking beer in a warm hotel. (Yay infrastructure!) I’m in a daze, and for the first time in my life experiencing the severe squeeze of altitude. I’ve hiked at higher elevations but this is the highest I’ve been on skis, and I ponder what it must be like to feel this physically compromised in a hairy spot — ice-axing up a chute, say, or navigating a knife-edge ridge in a gale. I’m lost in these musings, shuffling uphill and staring at the ground, when I almost run into Dav.

“Dude, you did it!” he yells. I look around, and it’s true: Every molecule of Quandary’s mass now lies below us. I’m still cold and weary but a rush of euphoria sweeps those symptoms aside.

A few yards away we snap a selfie on the mountain’s high point, and assess our next move. The snow has let up but we’re still cocooned in the intractable cloud.

Davenport swivels his focus between ground and sky and within a minute renders his verdict: “We’ll ski down the route we came up,” that is, not down a “sick line” (steep, aggressive slope) he’d mentioned earlier, a descent that includes 2,500 vertical feet of sustained 40-degree pitch.

We peel off the climbing skins, click into our bindings and pause. As he does on every summit, Dav invokes his 10-second rule — a hyper-focused check of zippers, clips, packs and bindings to make sure everything is as it should be for a backcountry descent. We skitter across the wind-scoured summit back to the top of the gully.

“Okay,” says Davenport, “stay near my tracks and hopefully we’ll be able to see something soon.”

Within a few turns in the buttery powder I loosen up with the realization that the hard work is over, I’m no longer wrestling gravity and, as a bonus, I probably won’t die today. I want to stop to watch the legend ski but I wouldn’t see much of him anyway, so I keep arcing through the weightless snow, lacing each turn with added caution, a necessity in an environment where a binding blowout or minor injury can transform adventure into catastrophe.

At the bottom of the gully, we cut right to avoid a band of cliffs and exposed scree — a zone dubbed “gnarnia” on one Quandary chat board — and traverse, finally, into decent visibility and another pitch of untracked snow.

I barely notice when we pass the first tree, signaling the beginning of the end, a mere 35 minutes after leaving the summit. Davenport beckons me to follow him on a quest for one last shot of powder. But we’ve pushed our luck too far and find ourselves stranded on a slope of rock diabolically concealed by a few inches of snow.

Ah, well. Mountains don’t come with guarantees, nor should they. We pick our way down, wincing with every scrape of ski on rock, before sliding past the trailhead and to the car.

Our 3,300-foot climb and descent — about the equivalent of one tram lap at Snowbird in Utah — had taken nearly four hours. (When I press him, Davenport says he could have done it in half that time on his own.) During my darker moments on the climb, I persevered with a mantra: “Just finish. You never have to do this again.”

Davenport, apparently, sees it differently. As we wind past the gingerbready facades of Breckenridge and down toward Interstate 70, he turns to me. “One down,” he says. “Fifty-three to go.”

Briley is a writer based in Takoma Park. His website is

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If you go

Where to stay

Limelight Hotel

355 South Monarch St., Aspen


This modern yet welcoming sanctuary, located two blocks off Aspen’s Main Street, has an airy, firelit lobby that doubles as a community gathering space and extension of the on-site bar and restaurant. Many of the amenity-rich rooms have balconies, and the hotel offers a menu of its own adventures, from fat bike tours and skiing with the Aspen Ski Patrol to discounted lessons. Rooms from $235.

What to do

Ski with Chris

Davenport is based in Aspen, Colo., but leads adventures around the world. He hosts week-long camps in Portillo, Chile, every summer, and will take clients on custom adventures in various destinations. Be ready to honestly assess your abilities. Camps from $2,975; custom adventures from $1,200.