It is famous for the Highland Bowl, which provides what some people consider some of the most intense, wild, and fun[weasel words] skiing in the state.

Rolling wide intermediate trails through thick lodgepole pine forest constitute most of the mid-to-lower mountain terrain.

On the skiers' right side is Steeplechase, an area of long and steep terrain with some runs reaching upwards of 45 degrees.

Views of the Maroon Bells, Pyramid Peak, Hayden Mountain, and the Highland Bowl greet skiers at the summit.

The B-Zones (for blue wax) face east and descend down the center of the bowl from the 12,392 ft (3,777 m) summit of Highland Peak.

The south-facing Y-Zones (yellow wax), are the steepest, with slopes as steep as 48 degrees, according to Aspen Highlands trail maps.

On March 31, 1984, ski patrolmen Chris Kessler, Tom Snyder, and Craig Soddy were completing avalanche control work in Highland Bowl.

A monument in their memory has been erected near the top of the Loge Peak lift above the ski runs named in their honor (Kessler's Bowl, Snyder's Ridge, and Soddbuster).

Just before the 2005–2006 season The Aspen Skiing Company completed work on the new fixed grip triple lift "Deep Temerity".

The $2.7 million project eliminated the lengthy trek out from the bottom of the Highland Bowl, the Temerity glades, and Steeplechase.