The Mt. Ascutney Ski Club cut the first trail at Ascutney in 1938. Skiers initially had to hike up the mountain to be able to ski down the trail, now known as Screaming Eagle. In 1946, Catharine Cushman, with the help of others, began to develop real estate on the mountain, in essence opening Ascutney as a ski area. It wasn't until the second year, 1947, that two rope tows were installed to take skiers up the mountain. The first groomer was bought in 1947, while snowmaking was installed ten years later, when the ski area was owned by John Howland. Kurt Albert is the only man to ski 24 straight hours at Ascutney to raise money for charity in 2001. When Summit Ventures owned Ascutney, they invested $80 million into operating the resort, but had to file for bankruptcy in 1990. After three years of closure, Steven and Susan Plausteiner from New York City bought Ascutney for over one million dollars. Improvements under the Plausteiners include snowmaking coverage being expanded to 95% of the skiable area and installation of a high-speed detachable quad chairlift in 2000 from the bottom of the mountain to a new, higher peak.
2010 closure
In 2010, rumors spread of severe debt and financial troubles on the part of the owners, the Plausteiners. In October 2010, the State of Vermont admitted that Ascutney Mountain had not yet filed for lift inspections, and the resort did not open for the 2010 winter. Despite the closure of the ski operations, the resort hotel at the base of the mountain, a Holiday Inn affiliate, continued to operate. Holiday Inn Club Vacations had no ownership ties to the ski operation. Following a protracted legal battle, Dan Purjes of MFW, the principal lien holder on the property, assumed ownership as the only bidder at an auction of the resort's assets in November, 2013. The high speed quad, known as the "North Peak Express," was sold to Crotched Mountain, which installed it in 2012. The Triple Chairs were removed in 2014 and sold to Pats Peak ski area in Henniker, N.H. On January 8, 2015, the ski lodge burnt down, and has since been demolished. In 2017, Pats Peak re-installed the Snowdance Triple Chair, a CTEC Triple Chair that had operated as backup for the North Peak Express Quad, as the Peak Triple to replace a 1962 GMD Mueller Double Chair. In late 2015, a group of local residents with help from the Trust for Public Land purchased the area, a total of 468 acres, with plans to reopen a smaller, community ski area, keeping much of it preserved as open space. It is now owned by the town of West Windsor, Vermont.