The Whaleback ski area was started in the 1970s, and operated continuously until 2001 when then-owner Timothy Herbert closed it. On 8 December 2004, Herbert sold Whaleback to Evan Dybvig, a former freestyle skier for the US Ski Team. The area is also jointly owned by Dylan Goodspeed and Frank Sparrow, both of whom have a skateboarding background, though Goodspeed is also the manager of on-mountain operations at Whaleback. In preparation for its reopening, $1 million was spent in renovating the area, which opened for the 2005-2006 ski season. Dybvig intended for the ski area to diversify its offerings into the freestyle sports market, including constructing an indoor sports facility. During the area’s first two seasons, poor weather hurt it financially, leading to a program announced in August 2006 where individuals could pay to either place a plaque on or paint one of the chair’s on Whaleback’s chair lift. The ski area currently employs between five and nine employees, and has a revenue of between $500,000 and $1 million per year.
Whaleback has 30 trails, spread over 85 acres (34 ha) of skiable terrain. 28% of the trails are rated as easy, 39% are intermediate and the remainder are advanced. The longest trail is 1 mi (1.6 km) long. There are two terrain parks, and 80% of the terrain has snowmaking installed on it. There are three lifts: a double chair, a magic carpet and a rope tow. The mountain’s base elevation is at 1,100 ft (340 m), and the summit is at 1,800 ft (550 m), for a vertical drop of 700 ft (210 m). Whaleback has an average annual snowfall of 110 inches (280 cm).