Windham Mountain covers 285 acres (115 hectares) in the northern Catskills, with 54 runs falling about 1,600 ft (488 m) from a 3,100 ft (945 m) summit to a base at 1,500 ft (457 m). Nearly half the terrain is intermediate at 48%, with 20% beginner, 19% advanced and 13% expert. A six-seat chair, two quads, two triples, a double and five surface lifts serve the slopes, and the Ikon Pass tie-in brings plenty of visitors from the New York City area at weekends and holidays.

Wheelchair, Upper Wipeout and Wedgie are among the trails you will see on the map, and Wooly Bear is a beginner slope that gives learners a gentle start. Six progressive terrain parks range from the small features of Wraparound Park to the bigger jumps of Whirlwind Park, so riders can step up gradually. Windham suits intermediates cruising long groomers, families, and freestyle riders who like a park progression. Advanced skiers can lap the steeper upper pitches, though the mountain feels more polished than rugged. It is a good fit for a day from the city.

The 2025-26 season at Windham Mountain ran from 28 November 2025 to 29 March 2026, a roughly eighteen-week season supported by average annual snowfall of around 100 inches. Extensive snowmaking supplements natural snowfall to support the resort's early opening and consistent conditions throughout the season.

Midwinter, from December through February, typically brings the most consistent conditions to Windham's intermediate-weighted terrain. Given the resort's roughly two-and-a-half-hour drive from New York City and its premium, family-oriented positioning, Windham draws substantial weekend and holiday visitation from the downstate metropolitan area throughout the season.

Following the April 2023 ownership change, the resort has pursued significant guest-experience investment, an approach that continues to shape its seasonal operations and positioning relative to other Catskills resorts. School holiday periods bring substantial family visitation given the resort's varied terrain and upscale amenities.

Specific event programming beyond standard operations is not confirmed in available resort information. Since the resort's renaming from Ski Windham to Windham Mountain in 2001, and its subsequent 2023 ownership transition, the mountain has continued building on more than six decades of Catskills skiing history dating to its 1960 origins as Cave Mountain Ski Area. Windham's premium, family-focused character remains central to its seasonal identity.