Timberline Lodge's terrain rises from a base at 4,000 feet to a summit at 8,540 feet, a vertical drop of 4,540 feet across 41 runs spread over 1,415 acres on Mount Hood, Oregon. Terrain splits 50 per cent intermediate and 25 per cent each for beginner and advanced, with no expert-rated runs, and average annual snowfall of roughly 464 inches, among the highest totals of any resort in the contiguous United States. The resort carries Powder Alliance affiliation and offers the longest ski season in North America, with skiing available all twelve months of the year on the Palmer Snowfield.

Timberline Lodge itself, a National Historic Landmark, is as significant a draw as the skiing, representing one of the finest surviving examples of Works Progress Administration architecture and craftsmanship in the country. The resort's exceptional 4,540-foot vertical drop and near year-round operating window set it apart from every other resort on Mount Hood. Its combination of historic significance and genuine high-elevation skiing makes it a distinctive destination even within Oregon's crowded Mount Hood ski corridor.

The lodge was constructed between 1936 and 1938 as a Works Progress Administration project during the Great Depression, with 80 per cent of its 695,730 US dollar building budget spent on labour. Around a hundred construction workers lived in a nearby tent city while building the lodge, with women weaving draperies, upholstery and bedspreads, hooked rugs made from strips of old Civilian Conservation Corps camp blankets, and discarded cedar utility poles hand-carved into newel-posts shaped as birds, bears and seals. President Franklin D. Roosevelt dedicated the lodge on 28 September 1937, calling it 'a monument to the skill and faithful performance of workers on the rolls of the Works Progress Administration.'

The lodge opened to the public on 4 February 1938, with a portable rope tow installed the following year and the Magic Mile chairlift opening in November 1939, bringing organised skiing to the mountain. Summer skiing and race camps began in 1956, establishing the year-round operating tradition that continues today. Adult daily winter tickets run from 89 to 109 US dollars, with a season pass at 899 dollars.