Established in 1957 by Nelson Pauly, John Fisher and Bill Northrup, the facility opened with four runs and one T-bar lift.

The resort is 52 miles (84 km) south of the Canada–United States border at Buffalo; Canadians constitute approximately one third of Holiday Valley's business.

[2] After a search for initial investors, in 1956 Robert "Bob" Stubbs lead a group founders that included Dick Congdon, John Fisher, and Bill Northrup sold stock in a parking lot in Ellicottville for $100 per share to open a ski area.

Due to the fluctuating climate in the area during the winter in the early and late season, the resort relies heavily on snowmaking technology.

This system automatically controls the amount and temperature of water it sprays, which snow machines on the mountains are running, and when they turn on and shut off.