We walked around Old Montreal for part of our day and I feel like it would be more fun any other time of year besides winter. There wasn't much going on besides skating and horse-drawn carriage rides. The skating was pretty good, just a bit busy. It's quaint with cobblestone streets, cute store signs, and nice views of the water.
Lots of little shops, art galleries, and cafes to check out. So a nice place to go for charm and walking--be sure to wear flats.