The Most Successful Secret in the Catskills--Jackie Kennedy skiing at Aspen. In 1961, the Kennedy family found something at Cave Mountain in Windham more elusive than a clear trail: privacy. While the world's cameras followed the First Family everywhere, Windham Journal editor Sidonia Palace ensured their time in the Catskills remained off the record. Palace prided herself on a self-imposed news blackout, protecting the family’s leisure time from the press. It remains a rare instance where local journalistic integrity trumped a national scoop, explaining why one of the most photographed families in history left almost no visual trace of their time on Windham’s slopes.
WINDHAM—In the early 1960s, a quiet revolution began on the slopes of what was then known as Cave Mountain. While the New York State Assembly had initially considered the peak for a state-run resort, it was a private group of investors—led by the Macomber family—who officially opened the Cave Mountain Ski Area in 1960. At its inception, Windham was not the bustling public destination it is today; it was an exclusive, mid-century enclave that served as a winter sanctuary for the Northeast's social and political elite.
The Kennedy Connection
Perhaps the most storied chapter of Windham’s early years was its role as a getaway for the Kennedy family. During the 1960s, the mountain’s private status and proximity to New York City made it an ideal retreat for Jack, Jackie, Robert, and Ethel Kennedy.
Local lore and historical accounts frequently cite the "Kennedy visits" as a defining era for the town. While Robert F. Kennedy was an expert skier who favored fast, aggressive runs, Jackie was often seen making cautious, graceful stem turns on the gentler slopes. Following the national tragedy of 1963, the family continued to use skiing as a way to return normalcy to the lives of the Kennedy children. These visits, often joined by other high-profile figures like Robert McNamara, helped cement Windham’s reputation as the "in-sport" destination of the decade, fanning a blizzard of publicity that transformed the Catskills into a winter rival for Vermont.
Expansion and Rebranding
The transition from a private hideaway to a regional powerhouse began in earnest in 1963 when the Sheridan family took over ownership. They introduced the mountain's first snowmaking capabilities, following close behind the Slutzky Family of Hunter Mountain in 1960, helping to pave the way for the miraculous new technology in the East—initially covering just 12 acres—and built the foundational ski lodge that would house generations of families.
The mountain underwent several identity shifts as it grew:
- 1981: Irv Naylor purchased the resort and rebranded it as Ski Windham, launching a period of massive infrastructure growth, including the addition of East Peak in 1987.
- 1993: The resort installed its first high-speed quad chairlift, a major technological leap for the Catskills.
- 2001: The name was simplified to Windham Mountain, reflecting its status as a premier four-season resort.
A Return to Exclusivity: The Windham Mountain Club
In 2023, the mountain entered its most ambitious phase yet. Under new ownership by the Beall and Kemmons Wilson families, the resort was rebranded as the Windham Mountain Club. This $70 million revitalization project is, in many ways, a nod to its mid-century roots as a private club.
Today, while still remaining open to the public, the "Club" focuses on a "luxury-first" experience, introducing uncrowded slopes, a reimagined culinary program, and high-end amenities like a Tom Fazio-designed golf course and a luxury spa. From its humble days as Cave Mountain to its current status as a world-class destination, Windham remains a foundational cornerstone of the Northern Catskills community.
