Hello Alex,
What a great dilemma to have - trying to decide between a great time of year and other great time to go to Disney World!
In October, you have
Mickey's Not So Scary Halloween, my favorite event at Magic Kingdom. Dress up with your favorite characters, Pirates, and Princesses for a night of fun. But if the white fluffy stuff is more your speed, Disney begins to celebrate the season with
Mickey's Very Merry Christmas Party. Outside of holidays such as Halloween and Thanksgiving (U.S.), crowd levels are really manageable. And same goes for weather. I know I really love the fall Florida temperatures when I've visited in the past. (Last December, Florida had unseasonably chilly weather but it was still warmer than what I had in Ohio so I was happy!) So really, it's a matter of which season you enjoy the most!
My family always enjoys staying at a Disney Resort. As a Resort Guest, you can take advantage of
Extra Magic Hours and of
Disney's Magical Express. Plus, my family always loves to make use of the
Disney Dining Plan too!
Hope this helps! Happy trip planning!