Peak viewing: Chris Davenport, left, and Simon Usborne

Simon Usborne explores Aspen old and new with the resort’s king of the mountains

Last year, while he was waiting for a window in the weather to launch an assault on the summit of Everest, Chris Davenport skied the mountain's fabled Lhotse Face. Eight inches of light snow had somehow bonded to the 1,000-metre wall of blue glacial ice, giving the American the chance to become one of the few men ever to have made tracks on the world's highest peak.

Last February, in a hotel basement, Davenport was gearing up for a rather less demanding challenge - skiing with me. For a boy who grew up watching the feats of men like Davenport on screen, it was a bit like booting up for a kick-around with David Beckham. Outside, as we clipped into our skis, I felt the need to impress him, but also to stay upright.

We were in Aspen, where Davenport, 41, lives with his wife, Jesse, and their three sons. The mining town turned ski resort, 200 miles west of Denver, Colorado, is become synonymous with glitz and wealth. Fur flies through the streets here on the backs and boots of Kate Hudson, Jack Nicholson and the Hilton sisters, as well as, increasingly, oligarchs and financiers. Money would pile up like snowdrifts on the sidewalks if many of them weren’t heated.

Last year, the Wall Street Journal named Aspen America’s richest town but if the folk who land their private jets here around Christmas make the place shimmer, it’s people like Davenport who make it special. He represents another scene here of people who come and often settle for the love of the mountains and the town’s peculiar charm: skibums, intellectuals, writers, rebels.

It started for Davenport in his early 20s, when he spent summers carving out runs in Snowmass, a short drive out of town. “I just strolled across the hills in summer with a chainsaw,” he recalls as we go up the area’s Elk Camp chair. Skiers today who make the short hike from the top of the lift would thank him if they knew he had a hand in creating Long Shot, a five-mile descent through glades. Sadly for us, there hasn’t been snow for days and it takes everything for me to match Davenport turn for turn (and this guy puts in a lot of turns) as he hops down moguls and hard-pack. Few around us know who the guy in the helmet is. As we ski into the lift line, we pass a woman wearing Davenport’s branded Kastle skis, which he designed. “Nice skis,” he says to the woman. “Er, thanks?” she says, bemused.

Before his chainsaw days, Davenport learned to ski on the sheet ice of his native New Hampshire, before heading west in search of downhill glory. Aspen became his hill and soon inspired him to switch from racing to big mountain skiing. He became the best: twice the world extreme skiing champion and, later, an accomplished mountaineer. He’s now an official ambassador for Aspen, showing it to anyone who wants to peer under its fur coat.

The night before, I had explored the town from my base at the Limelight Hotel, a mid-range (by Aspen standards) hotel. For a sense of old Aspen, I headed to the Jerome, the resort’s historic heart. Built in the 1880s, it boasted the first electric lights in the western states and a bar Gary Cooper and John Wayne would go on to get drunk at. During prohibition, the hotel  became notorious for the Aspen Crud, an illicit cocktail of whisky and vanilla ice cream made to look like melted snow. I had three.

The bar also served as an office for Hunter S Thompson, perhaps Aspen’s most famous resident. The late writer and counterculture legend lived a few miles outside town at Woody Creek, home to a different sort of establishment. The Woody Creek Tavern’s log walls could be supported by memorabilia such is the volume of photos and trinkets they support. They include tributes to Thompson such as campaign posters for the his failed bid to become the county sheriff in 1970. Have a margarita (he liked them for breakfast) and a rack of ribs.

Fancy Aspen asserts itself again back in town at the Little Nell, another five-star institution that hosts jazz nights at the Jas Cafe (Curtis Stigers played the night I was there). This town could suffer from a split personality but somehow the very grand and the grounded happily coexist. A millionaire might share a chairlift with the guy who served him last night at Matsuhisa, Aspen’s outpost of the Nobu restaurants. He might discover that the waiter is one of the best mountaineers in town who works two jobs to indulge his passion. And then they might ski a run and nobody would care.

Aspen Mountain itself is one of four areas that make up the resort (they share a skipass and shuttle buses). It offers terrific tree skiing, while Snowmass, where I skied with Davenport, has enough terrain to satisfy any ability. Buttermilk is good for beginners and has snow parks while Highlands has some of the best off-piste terrain. I hiked up from the top lift to 3,800m and the renowned Highlands Bowl, a vast alpine amphitheatre of steeps and the only place to find untracked snow in a dry spell.

The next day, it’s lunchtime and Davenport has to go. He shakes my hand and heads for bigger things (he spent the following month climbing and skiing 14 volcanoes in the Pacific Northwest in 18 days in a sponsored tour called “Ring of Fire”). As I ascend Sam’s Knob without him (ahem, it's a chairlift) a flock of finches devours seeds from a feeder placed there. Their increased appetite is a harbinger of snow here as reliable as any forecast; they know it’s coming so feed up fast before dinner disappears. Sure enough, I wake up the next day to find the sky filled with ping-pong ball flakes. I spend my last morning in Aspen alone but delirious, powering through powder that gets deeper with every descent.