Aspen Highlands is the one mountain in the Aspen chain that is so good, with such an endless menu of famous terrain, the skiing and riding eclipses the iconic town itself. This is the local's choice, a thousand-acre ski area that sits in its own little pocket of Maroon Creek canyon, away from the flashy crowds and the downtown hubbub. Both sides of the narrow ski area hold perfectly pitched 45-degree black diamonds that give way to easier glades toward the bottom. But the real crown jewel, and perhaps some of the best terrain in the world, is the wide-open steeps of Highland Bowl. It does require about 45 minutes of hiking from the top of the Loge Peak lift at 11,675 feet, but the reward is nearly 20 named lines so long your quads will give out before the bottom, each of which funnels toward Deep Temerity lift, which shuttles you right back to the top of Loge Peak.
Where to Stay: From the outside, Aspen Highlands's base area has the high-end feel you expect here, but the après crowd inside is more duct tape than diamonds, and there aren't a whole lot of hotel options. Still, to really soak up the experience, you'll want to stay in Aspen proper. The Limelight Hotel is a super family friendly and unpretentious place in the center of everything, and a shuttle ride from Highlands.
Insider Tip: Blinded by Highland-Bowl glory, everyone just hikes, head-down, straight for the top. Instead, drop off early into what's known as the Y Zone, insanely beautiful skiing that is largely ignored. Plus, it takes only 10 minutes to get to instead of 45.