Windham, NY is a tiny ski resort area. Off of Exit 21 on the NY Thruway, Route 23 (basically the only way in and out of Windham) reigns as the center of town. Wealthy weekend regulars come from Manhatten, Long Island, New Jersey, and Connecticut and usually own expensive trailside homes, condos in the Enclave, or houses past Main Street. Everyone ignores the shitty local houses. The racing and freestyle programs are very good, although to be honest the terrain sucksss. Adaptive is one of the best in the country (teaching mentally retarded kids to ski...kind of funny- and physically challenged kids.... also funny). Windham Mountain's base lodge has "the Wintergreen" where only the elite of Windham can belong, eat in the restaurant, have mahogany lockers with a gold name plate, and basically act like they own the mountain. the "3500 club" is for the normal weekend regulars (only the very rich, not the extremely rich). the CLC staff has the craziest parties. Ski patrol is full of a bunch of old guys that yell "slow down!" and no one listens. No one cares for locals because they're poor and live in the middle of nowhere. As far as restaurants go, Jimmy O'connors is the best to go hang out with friends, Millrock is a staple, and Brie and Bordeaux is for a fancy night out. Michael's Diner is only good for dessert, fries, and milkshakes. You only have 3 options for movies at the movie theater, but it makes up for it with the tables in one, antiques blocking the screen in another, and reclining chairs in the last. Windham is fucking sick, the people rock, the lodge rocks, the houses rock, and basically everything rocks. Its way better than shitty Hunter, even if all the trail names start with "W" (its endearing okay!) Only the rich, young, and beautiful are weekend regulars to ski at Windham Mountain. REPRESENT.
Friend 1: Hey do you want to come to my ski house this weekend?
Friend 2: Well where do you go?
Friend 1: Windham, NY of course!
Friend 2: Damnn.. you go to Windham?! You must be rich!
Friend 1: Yeah my house is on the mountain and I have a snowmobile, hot tub, 4 pairs of skis,go to the Wintergreen, and basically own a 2nd house 3x as expensive as your only house!
by i live off daddy's money April 27, 2009
A place in the Catskills where you get stuck when you have given up on life in reality.

If you live there you are indentured servants to the whims of the citidiots who enjoy the area for the recreational sport of spending money.
Hi, I'm from Windham, ny and all I can talk about is how much I hate the citidiots who are the economic backbone of the town.
by your customer service provider April 25, 2011

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