The first trail was cut at Sugarloaf in 1950 by the Sugarloaf Mountain Ski Club and a group of locals known as "The Bigelow Boys". Led by Amos Winter, along with Stub Taylor, they transformed the mountain into what is today one of the largest ski areas in the Northeast. The founding of the mountain was called for by the US ski association. They hired Pheous Sprague to find a mountain in Maine. Initially, they planned to have the mountain on the Bigelow mountain range, but when Flagstaff Lake was made the plans had to be scrapped. Phin Sprague then found Amos and Stub which knew of a mountain called Sugarloaf. Many documents relating to the founding and early years now reside at the Ski Museum of Maine in Kingfield, Maine.