The company was founded in 1977 by Tim Boyd, two years after graduating the University of Missouri when he bought the Wildwood Golf Course in the suburban St. Louis, Missouri community of Eureka, Missouri for $250,000 with owner financing. In 1982 he added a ski resort (that would become Hidden Valley Ski Resort). Shortly thereafter he opened a ski-resort in suburban Kansas City, Missouri at Weston, Missouri (Snow Creek Ski Resort).
The company continued to expanding owning Paoli Peaks in Paoli, Indiana; Boston Mills and Brandywine in Peninsula, Ohio. In 2002 it expanded with Crotched Mountain in Bennington, New Hampshire. In addition it has long term leases on Jack Frost and Big Boulder ski areas in Blakeslee, Pennsylvania in the Poconos as well as Mad River Mountain in Zanesfield, Ohio.
In 2007, the company nearly tripled its revenue with the acquisition of Mount Snow in Vermont and Attitash in New Hampshire from the financially troubled American Skiing (which was owned by Oak Hill Capital Partners, a private equity company). The acquisition increased Peak Resorts ski visitors from 1 million to 1.7 million and revenue of $85 million.
The acquisition increased full-time staff to 250 full time employees (plus 6,000 to 8,000 seasonal employees).