Windham Mountain's summit reaches 3,100 feet, dropping 1,601 vertical feet to a base at 1,499 feet across 54 runs spread over 285 acres in the Catskill Mountains, roughly two and a half hours from New York City. Terrain splits 48 per cent intermediate, 20 per cent beginner, 19 per cent advanced and 13 per cent expert, with average annual snowfall of roughly 100 inches. Eleven lifts, including two quad chairs and one six-person chair, serve the mountain alongside one double chair, two triple chairs and five surface lifts.

Windham has cultivated a reputation as one of the Catskills' more upscale, family-oriented resorts, with substantial recent investment aimed at elevating the overall guest experience. The resort's proximity to New York City, combined with its premium positioning, has made it a popular choice for downstate visitors seeking a more refined mountain getaway.

New York's state assembly considered developing a state-run ski resort on the site, then known as Cave Mountain, in the late 1950s, but the project never advanced. Private investors instead purchased the land and opened Cave Mountain Ski Area in 1960, with ownership transferring to brothers Bob, James and Tom Sheridan three years later, who opened a lodge and introduced early snowmaking. In 1981, Irv Naylor, founder of Snow Time Inc., purchased the resort and renamed it Ski Windham, his third New York and Pennsylvania-area ski area alongside Ski Roundtop and Ski Liberty. The resort was renamed Windham Mountain in 2001.

In April 2023, Beall Investment Partners and Kemmons Wilson Hospitality Partners took majority ownership, with North Castle Partners, Cloverhill Group, and the McGuffog and Starker families remaining as existing partners. This new ownership group has pursued significant investment in the resort's facilities and guest amenities. Adult daily tickets run from 99 to 149 US dollars.