[Loco101]

I would add to check for what festivals are going on when you'll be there. Also see if there are outdoor concerts or if places will have outdoor entertainment. I've often enjoyed just the random things you'll find in Montreal that are going on without really much planning.

It's never boring walking along St-Denis Street or Crescent Street and finding live music. If you like jazz I recommend the Upstairs Jazz Bar and Grill (it's actually located downstairs in a building on Mackay Street just off Sainte-Catherine) for good drinks, food and jazz. The jam sessions are really fun.

If the weather is nice it's always fun to walk up Mount Royal and go to the Kondiaronk Belvedere (lookout) and take photos. It's a classic thing to do in Montreal.

Wherever you are there is almost always interesting architecture and details is so many things you don't see elsewhere.

I could recommend so many other things but I'm hoping a few others on here mention some ideas.