I have been to WDW in late October 5 out of our 6 trips (the other was at Christmastime), and it is my favorite time of the year at Disney! Popular rides will always be crazy, but crowds are low for Disney at this time of year, excluding Halloween Party nights that are close to actual halloween. The weather is typical florida, HOT. 3 of our years we had record breaking heat in the 100s, but usually just upper 80's and 90's. The fall decorations are just beautiful, and its fun to see some of the characters in costumes as well. I would highly recommend it!