Skiing in the late nineteenth and early twentieth centuries was a different experience from what it is today. Long, heavy skis had simple strap bindings that attached to any boot. Instead of two poles skiers used only one to balance and to brake. There were no downhill trails and because turning wasn’t easy skiers preferred gently rolling open fields. A few adventurers and pioneers did ski in the mountains, but one trip down usually required a day of arduous uphill climbing. Reportedly the first skier to come down the Toll Road on Mount Mansfield was Dartmouth College Librarian Nathaniel Goodrich in 1914.
As the sport of skiing became more organized, equipment and clothing became more available and specialized. Competitions were set up, but the events were primarily for jumping and cross-country challenges rather than for downhill skiing. Brattleboro became famous in the 1920s as a ski-jumping center.

As it became possible to get to the mountains, downhill skiing became more popular. In 1933 the Civilian Conservation Corps began to cut trails on state land on Mount Mansfield, and a rope tow was installed in 1935. The first ski trains from Boston and New York began running in the 1930s. The Mount Mansfield Ski Club organized the first ski patrol in 1936. By 1940, in addition to Mount Mansfield other ski areas included Big Bromley in Manchester, Hogback in Marlboro, and Pico in Killington. Stowe, which initially depended on barns, spare rooms, and attics to house the weekend crowds, soon began to develop a lodging industry to accommodate the growing number of skiers.

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