Aspen

Aspen has four ski mountains (Aspen Mountain, Aspen Highlands, Buttermilk, Snowmass) and a reputation for being exclusively for the ultra-wealthy that is both accurate and slightly misleading. The skiing on Aspen Highlands is some of the best in the country — Highland Bowl at the top is a hike-to backcountry experience above 12,000 feet — and Snowmass is a complete mountain resort in itself. The town of Aspen (Victorian mining-era architecture, population 7,700, median home price $6 million) has excellent restaurants, good art galleries, and a bar scene that functions at 2am on a Tuesday in January. The downside is that staying in Aspen is expensive in ways that require advance mental preparation — $500/night for a modest hotel room, $30 for a cocktail. The upside is that once you've paid for accommodation, skiing four mountains on one pass makes the daily value proposition quite good.