Axiom2001, I would go in September. This year, it was a hot summer, so Montreal saw temps in the 70s and 80s all month (which is unusually high, normally in 60s/70s) but October it was mostly in the 50s. As far as gay hotels, the gay area is centered around St. Catherine Street form Berri-UQAM to Papineau. If you search priceline, you can select the "montreal downtown- latin quarter" for hotels. If you like chain hotels, then the Governeur is in the area, and a Marriott Fairfield will be opening in Dec. There are many B&Bs along with Air BNBs. You can use trip advisor and search Montreal Gay village , then click on restaurants to get some ideas/reviews on food in the area. I can't help much on the culture side, I spend my time in the bars , St Catherine, or the Casino when I go.