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History of Windham Mountain

How Windham Mountain Evolved from Cave Mountain.

The idea of a ski resort in the Northern Catskills was introduced by a New York State legislative committee in the late 1950s. They considered developing a state-run resort on Cave Mountain, just off Main Street in the Town of Windham. Although this project never advanced beyond the discussion stage, the idea took hold and a group of private investors purchased the land for a ski area in 1960.

During its 55 years of existence the Resort has become renowned for superb customer care and attentiveness to its guests.


Historical Photos 1960

Private group purchases land and opens Cave Mountain Ski Area, run by the Macomber family.


Ski lodge built by Avalanche Corporation after ownership transfers to Tom and Bob Sheridan. First snowmaking effort covers 12 acres.


Wonderama Trail and new lift added.


Private Windham Mountain Club established. Skiing celebrities Stein Erikson and Suzy Chaffee are regular visitors.


Residential development begins. Club members own 58 properties on the mountain by 1975.


"B" lift installed on Wheelchair.

Snow Time purchases resort and renames it Ski Windham, snowmaking covers 90% of resort.

1981 Ski Windham brochures

Disabled Program (Adaptive Sports Foundation) begins and "F" lift constructed.


Wheelhouse Lodge built and "D" lift added.


Brainard Ridge Townhomes, Windham Mountain Village add more housing on mountain


New "G" lift accompanies expansion on mountain's East Peak.


New 72,000 square foot base lodge built, Children's Learning Center opens.


Tubing on the snow


High Speed Quad installed on "A" lift to whisk skiers up the mountain in record time.


Windham Arms (Winwood Inn) acquired to expand services and offer lodging to guests.


Pond installed, increases snowmaking.


Night skiing and riding extend time on the mountain, terrain park opens.


Mountain Top Adventure Park opens for tubing and Wanderer Trail built on East Peak.

The name “Ski Windham” is replaced by “Windham Mountain,” reflecting the resort’s commitment to the enjoyment of all snow sports on the mountain. New lodge at tubing park constructed.

2001 Lodging

Third lift installed at tubing park and 3500 Club expands space.


Fully-automated snowmaking arrives.


New Adaptive Sports Center building, "K" lift and larger beginner area debut. Enclave Club Condominiums open in Fall.

A group of local investors organized by longtime resort president Dan Frank purchases Windham Mountain and begins planning for more new mountain improvements.


New owners Windham Mountain Partners invest over $5 million - the single largest year of capital improvements at the resort - for three new chair lifts (including a high-speed, detachable quad), three new trails, an ice skating center and the new Trail's End Tavern & Grill.


Another $4.75 million is invested in Windham's base lodge - including exterior improvements, an expanded retail shop, new cafe, improved firepit area, new barbecue and grill on the patio and The Club at Windham Mountain.


Windham Mountain enters into the 50th year in operation. The snowmaking pond is expanded to allow snowmakers to produce more snow in a shorter period of time.


Windham Mountain invests $4 million focused on upgrades to snow grooming and snowmaking operations that improve the on-snow experience - including 2 grooming tractors and a new pumphouse and pumps on the Batavia Kill.  Also added is the Competition Center and the new trail on the East Peak Wintuck.


Windham Mountain Resort invested $7 million in capital improvements for the 2013-14 season. Projects include Whisper Run expanded beginner area, a new entry and modernized parking lot, Windfall a new trail on the Resort’s west peak along with Whataride Glade. Investment in snowmaking infrastructure, construction of a new expanded compressor and maintenance building and the addition of Windham Country Club.