In the winter of 1937-1938, in cooperation with The Seattle Times, the Chicago, Milwaukee & St. Paul Railway established the "Milwaukee Ski Bowl" at Snoqualmie Pass. The railroad cashed in on the region's budding interest in outdoor sports, and the initial lack of adequate highways, to support winter day trips to the Cascades. Its catch phrase, "Let the Engineer do the Driving," highlighted the package's ease and convenience.
The ski bowl, a glacier-formed valley, was a set of five ski runs located on Milwaukee property at the top of the pass between the east entrance of the Snoqualmie tunnel and Hyak. The runs were named for Milwaukee's best known trains: the Hiawatha, Chippewa, Arrow, Pioneer, and Olympian. Trains ran on a two-hour schedule every Saturday and Sunday, leaving from Union Station in Seattle. The recreation package was more popular than the company expected. Daily use exceeded 1,000 passengers, and the Milwaukee brought in extra coaches.
The Milwaukee discontinued the Ski Bowl during World War II, but in the winter of 1946-1947, reinstated the program. The railroad improved the ski area by expanding both the runs and the ski lodge. Although the lodge provided no overnight accommodations, its amenities made it "the outstanding ski headquarters of the Northwest." Guests were provided with a dining room, fireplace, rumpus room, ski shop, modern plumbing, lounge with fireplace, easy chairs, card tables, a dance floor, and a cafeteria restaurant.
In December 1949, a fire consumed the ski lodge, and the project ended. The Milwaukee discontinued the run and decided against rebuilding, due to the increasing expense of operating the trains, and the growing number of competing runs along the newly completed Highway 10 running through Snoqualmie Pass.