Before we had ever even contemplated moving to Montreal, we had planned (and then forgot about) the Tour la Nuit, part of Velo Quebec's annual bike festival. It's a 20km ride around the city after dark, accompanied by about 14,000 other people. We did last year's ride, almost immediately after our move, and it was a great way to get to know parts of the city I will probably never visit otherwise. This year's route was a little more central - leaving from our house (win!) and traveling through old montreal, and some of the south-west parts of the island, near my office and then back up to the Plateau for the finish.
If you haven't contemplated doing a ride like this - you should! It's designed to be pretty easy (there were little kids, senior citizens and all kinds of other folks tackling the route) and since it's not a race (seriously - it takes at least an hour to hit the start line) you can bike at whatever leisurely pace you want to cycle at.
Now that I've got two years of this ride under my belt, maybe I'll be ready to tackle the 50km route next year.