Windham's luxurious base lodge, valet parking, and general "toniness" may obscure the fact that the mountain offers some fine skiing and riding.
With 1600' of vertical and a 3100' summit, Windham is a real mountain with some serious trails. But that just gives you something else to appreciate aside from the first-rate facilities. (The well-appointed base lodge is heated by the excess heat generated during snowmaking operations. Windham was one of the first and remains one of the few resorts to heat a major structure in this way.) The vertical is served by seven lifts including the high speed Whirlwind Quad.
Beginners start at Wooly Bear and work their way up to more challenging terrain. Wonderama is a classic green-circle trail, and the Whiteway Triple serves the long and gentle White Way and What's Next.
Windham's 39 trails lean mostly to the intermediate side of things, and there are some terrific offerings in the bunch. Wanderer meanders for a mile and a half from the top of the Why Not Triple, affording nice views along the way (this is, after all, the northern Catskills) and snowmaking along its entire length. Solid novice skiers and riders will also enjoy this impeccably-groomed trail. Or try the mountain's longest trail, Upper and Lower Wraparound. A straightforward upper section is followed by a couple of steeper drops that mark a couple of big turns before Wraparound mellows out into a long cruiser. A bit more direct and a little tougher is Upper and Lower Whistler, a good warm-up before you head to Windham's tougher stuff.
From the black diamond trio of Why Not, Wing'N It, and Wicked off the Why Not Triple to double blacks like The Wall (bumps), Upper Wolverine (groomed for big GS turns), to Wedel (yet more bumps) advanced skiers and riders will find plenty to keep them amused at Windham. There are several gladed areas (all black diamond terrain) and even a couple of retro trails, including Old Wolverine (one of Windham's first trails) and Upper Wipeout. Both are natural snow trails, but 97% of the mountain's terrain is covered by snowmaking - and Windham makes a lot of snow.
A big half pipe and a well-thought-out park are available, and several mini-parks dot the mountain. And there's a lift-served tubing park. Windham leaves the lights on three nights a week most of the season and every night during a holiday period, with terrain available off the Whiteway and Wonderama Triples and the Wooly Bear surface lift.