make sense to travel from Montreal-N.Y. late October and into November?

I know that no one can predict the fickle (and sometimes mean) weather gods. Just trying to figure out whether we'd be wasting a lot of money doing a cruise during that period. Maybe the answer is just to flip a coin and if it comes up "go," just hope for the best. (I do not like very cold weather nor very rough seas.)

I would not do it. The leaves will mostly be off the trees and some seasonal attractions or restaurants in smaller places will be closed. The weather could be cool and sunny or it could be rainy.