Aspen sits at 2,400 meters in the upper Roaring Fork Valley, surrounded by some of Colorado's most dramatic peaks. It started as a silver mining town in the 1880s, went bust, and reinvented itself as a ski resort after World War II. Today it is one of America's wealthiest small towns, and the prices reflect it.
The skiing across Aspen's four mountains is genuinely excellent, with terrain ranging from gentle groomers at Buttermilk to the steep moguls of Aspen Highlands — plus the in-town vertical of Aspen Mountain and the family-friendly acres of Snowmass. In summer the valley opens up for hiking, mountain biking, and fly fishing, with wildflower-covered trails running in every direction, anchored by the iconic Maroon Bells. The town itself is compact and walkable, with a surprisingly strong cultural side built around the Aspen Music Festival, the Aspen Art Museum, and the restored 1889 Wheeler Opera House.
Aspen is expensive, no question. But the mountain scenery is spectacular, and the surrounding valley offers some of Colorado's best day trips into old mining towns, hot springs, and wine country — from the ghost town of Ashcroft and the long drive over Independence Pass to Hunter S. Thompson's old hangout at the Woody Creek Tavern.