Aspen has been a famously exclusive getaway since the 1950s, and it’s no mystery why this town of just three and a half square miles has drawn such a diverse crowd of converts. Unlike some mountain towns, Aspen (population: 6,607) banks on its summer weather, which is almost unnaturally bright and clear with zero humidity. It swells with attendees of its well-choreographed sequence of festivals: JAS Aspen Snowmass, the Food and Wine Classic, the Aspen Ideas Festival, and the Aspen Music Festival. And while the population of well-heeled summer residents (David and Charles Koch, Leonard Lauder, David Geffen, Mort Zuckerman) continues to grow, it also manages to blend seamlessly with the seasonally employed hiking guides.