Which holiday would be least painful?

Airfare is usually sky high with Thanksgiving week. Not sure how you are traveling to get there. This would still be my choice but costs are up with resorts, too.

Thanksgiving week you get the Christmas decorations. You get MVMCP for an extra cost. There are special events in Epcot like the storytellers in World Showcase and the Candlelight Processional. The resorts are decorated so beautifully. Especially wonderful is the Grand Floridian. The Grand Floridian even has a small orchestra doing Christmas music in the lobby.

I agree with the others that the crowds are not the worse. I think that's partially true because many families are celebrating that holiday at home or at relatives.
 
I love going at Christmas, but we are late nighters rather than rope droppers, MK between midnight and 2-3am is amazing.
 
I'm a teacher, and we went last December just for three nights (17-20). I had to take two days off of work (the two days before Christmas break), but that was fine with me! We got Disney done before actual Christmas and I still had plenty of time to chill out before school started back. Our trip was short because we were sparing no expense and doing it up right (Grand Floridian, MVMCP, Candlelight Processional dining package, Jingle Bell, Jingle Bam dessert party). Plus, I have a lot to tend to here at home (horses and dogs to be cared for) and hate leaving that burden on someone too long. But without that, I think five nights through the 22nd would have been wonderful. It is SO festive!

Of course, you'll get the Christmas festivities and splendor during Thanksgiving week too. I just like having some down time at home after a vacation to recover and relax before heading back to school/work.
 

So I looked at crowd calendars from last year and predictions for this year and it looks like Columbus Day weekend and Thanksgiving are pretty similar in crowds. So it might be a matter of when I can get a cheaper flight or we just drive 15 hours before Thanksgiving...

We've done mid-November (before Thanksgiving) and the Christmas Party and LOVED the decorations and the weather. We've never been to the Halloween party.
 

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