We have been going this same timeframe since 2007. We usually check in on the Saturday before Columbus Day weekend, then leave the Tuesday after Columbus Day (usually 10 nights). The first weekend has great crowds, and they don't usually start getting heavy until the Friday of Columbus Day weekend. That was the case for many years anyway. When we went in 2013 the crowds were super heavy almost the whole ten days! It was crazy! We went to
Disneyland last year in lieu of our WDW trip, but I had several friends there and they said it was pretty busy. Sadly, I don't think October is a coveted time to travel anymore with so many school systems going to a modified year round schedule with two week fall breaks (like ours). The weather is usually really good though, so I guess it isn't all bad

We will probably continue to travel then though as it's still better than most summer crowds.