Wine Expert Mark Oldman Drinks from Stiletto at Aspen Food & Wine Classic

Mark Oldman drank wine out of a high-heeled stiletto shoe.

It wasn’t just a gimmick for the cameras, though the photographers at Paepcke Park certainly caught it. It was Oldman’s 20th Food & Wine Classic in Aspen, a milestone that suggests a certain endurance, a certain willingness to stand in the Colorado sun and perform the rituals of taste for an audience that has learned to expect the unexpected. The date was Friday, June 19, 2026, and the air in the park held that specific, thin sweetness of late summer in the valley, mixed with the clatter of glass and the low hum of conversation that defines these gatherings.

This is the reality of the event that makes the drive up the valley worthwhile for many locals, even if the ticket price keeps the casual observer at bay. The Food & Wine Classic isn’t just a series of seminars; it is a sensory assault on the senses, a week-long festival that transforms the town into a playground for the palate. And this year, the transformation was already in full swing.

At Paepcke Park, the scene was one of organized chaos. Oldman, the wine expert whose career spans decades of teaching folks how to taste, led a seminar that drew a crowd. You could feel the attention in the room — or rather, in the open-air park — as he spoke, his voice cutting through the ambient noise. But it was the visual oddity of the stiletto that lingered. Why a stiletto? Perhaps it was a nod to elegance, perhaps to absurdity, but it was undeniably Aspen. It was a statement that here, tradition is flexible, and humor is a garnish.

Just a short distance away, at Wagner Park, the first grand tasting was underway. This is where the spectacle truly unfolds. Guests wandered between tables, glasses in hand, sampling offerings that ranged from the local to the exotic. The treats from Gateway Canyons Resort and Spa in Gateway, Colorado, were laid out with care, waiting for guests to indulge. You could see the liquidity of the moment, the way wine was poured, the way bottles were examined, the way people leaned in to compare notes.

It’s worth noting the geography of this event. We often think of Aspen as an island, isolated by its mountains, but events like this bridge the gap. The presence of chefs representing Charleston, South Carolina, in the high country is a reminder of how interconnected our culinary world has become. These weren’t just local vendors; they were representatives of a city known for its own rich food history, bringing their flavors to the Western Slope. It’s a cultural exchange that happens not in boardrooms, but over shared plates and poured glasses.

If you look closely at the photos from the day, you see the texture of the experience. You see a man looking over liquor bottles, his expression one of critical appraisal. You see the casual elegance of guests mingling, the crisp white shirts contrasting with the green of the park. It’s a scene that feels both exclusive and inviting, a paradox that defines Aspen’s approach to luxury.

The event is more than just drinking and eating. It’s a social contract, a way for the community to come together, to celebrate the abundance of the region, and to indulge in the simple pleasure of good company and good wine. As the day wore on and the light softened, the energy didn’t wane. It shifted, settling into a comfortable rhythm of conversation and consumption.

When you leave Paepcke Park or Wagner Park, you carry the taste of that day with you. It’s not just the wine, or the food from Gateway, or the charm of Oldman’s stiletto. It’s the feeling of being part of something larger, a tradition that has been going on for twenty years and shows no sign of stopping. It’s the knowledge that for one weekend, the valley is a place of abundance, of connection, of shared experience. And that, perhaps, is the most valuable tasting of all.