Tom,
Montreal is renowned for its restaurants and night life.
Check out Crescent Street for restaurants and St. Catherine Street for shopping - both downtown. Both of these streets are in the downtown area, but generally you won't have to walk more than a few steps to find a restaurant.
You might also check out Old Montreal which is where the old port of Mont Royal was established. It has cobblestone streets, great restaurants and lots of shops. It's within walking distance of downtown.
The Just for Laughs festival is on beginning July 15 for 10 days. I know there are lots of outdoor shows and you can check out
www.hahaha.com.
Hope you have a great time.
Love, Anna