It's during a morning gondola ride up Aspen Mountain when I overhear a woman talking about a shapely model hooking the ageing owner of one of the hottest restaurants in town.
"Another Aspen success story," she adds, nodding sagely.
"That's nothing," responds the gentleman opposite, who outlined the shame a sexagenarian friend had felt after he'd lied about his age while trying to woo a younger woman.
"You mean, you told her you were in your forties?" the gentleman had asked him.
"No!" the friend replied. "I told her I was in my nineties."
Aspen is brimful of tales about leggy mistresses stalking sugar daddies around the bar inside Cache Cache, and of gold-digging cougars loitering by the dance floor of the members-only Caribou Club. It's a story that's retold the world over: the young and beautiful snaring the rich and powerful. But for every story about billionaires pushing out millionaires, or how you need three homes or three jobs to live in Aspen, there are others countering those arguments.
Aspen remained firmly grounded until the jet-setting crowd discovered it in the 1970s, bringing rampant development and spiralling real estate prices with them. Left-leaning townsfolk attracted to the place's counter-cultural attitudes were galvanised into action, spearheaded by gonzo journalist Hunter S. Thompson's tilt for county sheriff on a Freak Power ticket. Housing was subsidised so that rank and file workers could afford to live there, stringent building restrictions were applied and transport improved. From that point forward, the Haves and the Have Lesses have shared an uneasy alliance that refuses to budge.
"The wealthy people have a few seats at the front, but they're not driving the bus," says Aspen historian Tom Egan. "Some people come to Aspen and let it change them, others come to Aspen and want to change it. Aspen's always going to change. But it needs to happen organically."
It's courtesy of this mindset that Aspen has managed to remain more affordable than its reputation suggests. The four mountains – Aspen (Ajax), Highlands, Buttermilk and Snowmass – cater for all levels of expertise and are connected by a bus network that doesn't cost a cent.
Rise early enough and you can even ski Aspen (daily) or Snowmass (Wednesdays and Fridays) all by yourself – almost. First Tracks allows skiers and boarders the chance to tear down untracked snow 30 minutes ahead of the crowds. For free. All you have to do is add your name to a list the night before then turn up by 8am.
For those new in town, Ambassador Programs on each mountain include orientation tours under the guidance of a resident ski instructor, as well as goodies such as coffee, cider and energy bars. Wednesday is Guest Appreciation Day on Highlands Mountain, where hot dogs, muffins and parking are given away.
Free cups of Lavazza coffee are dished out at the base of each mountain daily, though if American coffee doesn't cut it for you, head to VICTORIA+co opposite The Little Nell hotel. The cafe owners hail from Melbourne, where they know how to make good coffee. For the cheapest breakfasts in town, go to Jour de Fete, opposite Chateau Dumont.
Come night time, there's no shortage of pricey restaurants in Aspen. But you can sit at the bar in Matsuhisa or The Wild Fig and pay half the price of the person sitting at a table next to you. Locals do it. Why not you? Alternatively, there are Thai and Italian restaurants, and a selection of greasy spoon diners where you can order burgers and buffalo wings for the price of a cholesterol test.
It will cost you nothing to enter the Aspen Art Museum. And the Aspen Centre for Environmental Studies around Hallam Lake is completely gratis, despite being surrounded by celebrity neighbours. Up on Aspen Mountain, you can join outdoor yoga classes at the Sundeck in front of one of the most stunning alpine views you're ever likely to see for just $5 a session. If that doesn't inspire you, nothing will.
The Sundeck is one of more than 150 bars and restaurants spread across Aspen and Snowmass villages, and not all are high end. The Red Onion opened at the tail end of the silver mining boom and is Aspen's oldest bar. It is right in the centre of town in Cooper Avenue, where a pop-up Tesla showroom launched next-door last winter. Mondays are open-mic nights and there's live music every weekend.
Aspen's longest happy hour specials are at the four-star Limelight Hotel on Monarch Street. The flight of four beers on offer while you listen to live musicians performing most winter afternoons is a bargain at just $4.
If you'd rather imbibe at the source, trot down the road to the Aspen Brewing Company on Hopkins Avenue. Beware the Cougar Aged Blonde though; it's not nearly as appetising the morning after.
Travelplan has a great variety of Aspen Snowmass ski packages including discounted accommodation, lifts and airfares. Visit TravelplanSki.com or call 1 300 SKI SKI.
Mark Daffey travelled courtesy of Travelplan