Does anyone know when Windham typically opens? Also, any recommendations on child friendly hotels there?

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They usually try to open for Thanksgiving weekend, but it's very dependent on if the weather is conducive to snowmaking. I know that the NJ ski council has a "warm-up" day on December 6th, so they'll try even harder to be open for that since it's a prepaid event.
Not sure about hotels. There's not a lot on the road going up there. Most of the chain hotels will be near the NY Thruway. But there are a few in the nearby town that would probably be fine; you may want to call the hotels about any specific concerns you might have.

Thanks NJJohn! Do you two ever ski there?

__________________
Life is not measured by the number of breaths you take
But by the number of moments that take your breath away~

I have been there a few times. It's a bit farther to go than Belleayre (our usual NY day-trip area) but it's not as crazy as Hunter gets on a weekend. In the past they don't seem to have been aas aggressive with snowmaking as other areas, so I have been disappointed with the amount of terrain open. But when they are at 100% it's a fun mountain.
Looking at their website, the Winwwod Inn is closest and seems to cater to families since they have a game room and a small movie theatre. Other local lodging is described pretty well, so you can see what places would be kid friendly (obviously not someplace described as being filled with antiques). Sorry I can't give you any first-hand knowledge, but this is a day-trip area for us.
I can certainly recommend Belleayre. One nice thing about it for beginners is that it's a "layer cake" configuration, with the lower slopes being all greens with their own lift and the blues and blacks being on the upper part with 3 lifts serving those trails. Keeps the different levels seperated and there's less anxiety for beginners.

I grew up skiing Hunter, Windham, the defunct Big Vanilla, etc. So, the caveat is that I haven't been around for early season skiing there in close to 20 years. I've always thought of Hunter as opening up the earliest (or at least having the best coverage) among the Catskill resorts right off the Thruway. Thanksgiving seems like an ambitious target barring a snowstorm, and I would think that early Dec. is more likely. That region is very hit or miss and dependent on there being consistent cold weather. Is there any way you could take the kiddos to Vermont instead? If they've been skiing out west they're going to be royally disappointed with early season Catskills skiing. (I know, I echoed NJJohn a lot in this post....)

Mindy:
Pequenita pretty much hit the nail on the head when she said that anything early season in the Catskills is dependent on having consistant cold weather to make snow. I have had good conditions at Windham over Thanksgiving weekend, but 2 years ago they didn't have much of anything until the end of January. If you want to give me some details of what you are trying to put together (you can PM me if you want) maybe I can make some suggestions. I actually don't know where you live, so I don't know if this is a short or long trip, something where you are coming from out of town, how old the children are and how much experience they have, etc. I'll help anyway I can if you can give me some more info.