For the Quebec challenge on June 14th, you do have to register, and not sure if last minute you'll have some spot left. And you also have to pick up your stuff on the 13th (Friday). Nothing can be picked up on THE day.

For the rest, I think you'll be just fine riding by yourself (or if you find a buddy). My husband is into club twice a week, but I'm not. I like to do it at my own speed and no pressure. hihi So many roads and bike paths (although weekends are a bit nuts with kids, dogs, strollers, etc) are available at under an hour away from downtown Montreal. And quite a few big hills if you're up for it (Camillien-Houde, Mount-Royal) right in Montreal - almost downtown. Never (and will not) did those but heard they were tough.