I plan on visiting Montreal in the summer (in NYS, you can cross the border with an Enhanced Driver's License, which is a ton cheaper than a passport).
Are you planning on writing a recap/review of your visits to Canada, and Vermont?
If so, I look forward to seeing what you think is worth a visit!
Enjoy your trip :)
I know how you feel! We drove from NY to South Carolina a few years ago, and I was so excited about every single thing, even when we were driving.
I can't wait to venture out even farther :)
Then I'd suggest trying to see every little bit you can. :) I used tripadvisor to plan my daily activities out. I wanted to make sure I grouped them all together since the city is pretty large. I also went through the Labyrinth on the pier, which was kind of fun for a little while but I got so turned around that I befriended a family to help me get out. Haha. There's lots of fun/cool/different things to see. And maybe they have some winter-related activities/things to do and see.
You can walk around underground in the main newer bit of the city, which is kind of cool. I got lost in the underground mall/food court on my way out. I walked or too the subway thing around the whole time.