We just took our kids for the first time in February and already want to go back! We want to take advantage of the savings while our daughter is still 2 
Our tentative plan is to go from Thurs 9/24 - Tues 9/29.
I just checked the TP crowd calendar and it looks like relatively low crowds on those days - but I’m wondering if there will be a spike because it’s Halloween season AND that is the first weekend of Food & Wine Fest.
Does anyone think those events mean that the current crowd levels could change significantly from what they show now?
(Starting from Thurs through Tues, the resort-wide levels currently read: 4 - 2 - 4 - 2 - 2 -1)
I had someone go there that weekend last year. It was their first time in Disney and they LOVED it. They said the wait times and crowds were perfect and they loved walking around F&W.
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I believe that Halloween and F&W are taken into account. If you’re in doubt there are other crowd calendars available, compare a few so that you’re comfortable, but from everything I’ve read here, that’s a great time to go.
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One other thing to bear in mind is that the touring plans crowd calendar is based on wait times as opposed to number of people. It might feel more crowded in Epcot because of F&W as there will be more people there, but as they tend to be focused on eating and drinking there isn’t the same impact on ride wait times.
DW and I are going about that same timel. Really looking forward to the Halloween party and F&W. Pretty sure the crowd calendar is right except for the actual F&W crowd as @BigPetesWife mentioned. Should be a great time to be there other than weather still being a bit muggy, but I live in Alabama so I’m, pretty used to that kind of weather.
I went for my first visit during that week in 2014. In Epcot, I found that going during the week was not at all bad (I think I went Wednesday or Thursday), but I popped back in on Saturday for lunch, and the park was mobbed. A lot of locals go to the park on the weekend for the festival.
As far as I can tell, Halloween does not create too many problems, but keep a weather eye on the dates for the Halloween parties in MK. Because the park closes early on those days, people tend to flock to the parks on days without the party (I ended up hitting a particularly crowded day because of rain). On the other hand, if you don’t plan on staying out too late with the little one, I hear that the crowd levels are lower on days with the party because the park closes early. Based on that information, you may want to consider MK in the morning to early afternoon, and dinner at a resort or park hopping elsewhere.