Okay - back.
Eastern Townships - North Hatley is my absolute favourite town. How I adore it. I lived there for a couple of months about ten years after I graduated. and biked to Lennoxville (where I went to school) Nancy! The area is one big gigantic bike path. You'll see it called L'Estrie as well. Cantons de l'est. But beautiful towns - some ski areas and lakes.
Just putting all that out b/c if you're driving I assume you're coming up the 91 and crossing at Rock Island/Derby Line / Newport VT. So my area is right off there. Or were you planning on going over to the 89 to go straight to Montreal?
Okay - Montreal. Have you been? And forgive me is you said or said how long you were going for.
Downtown? You can walk everywhere. Or the Metro (subway) will get you places. Montreal and Toronto have underground walking/shopping as well if it's a crappy day.
There are a plethora of art galleries etc. Place des Arts holds many cultural performances.
There is a popular Jazz festival and just for laughs. Just for laughs is July I think. The Grand Prix comes to town so google that - brings big crowds.
Rue St. Laurent area is popular for nightlife.
Totally bilingual city - no worries about being lost.
Most love Old Montreal (artists, cobblestone streets, outdoor patios). Notre Dame is the big draw there. It's the most popular tourist area I would think.
Chinatown is right there as well.
Some love the port - I think it's okay.
Crescent Street for restaurants, clubs (jazz etc) and nice ambience. And is most popular with tourists.
Ste Catherine is the main drag/street for shopping downtown. Seedier in the east (that street only I mean). In general the east area of Montreal is more francophone - the west more anglophone.
Mont Royal has outstanding lookout area over the city and park area.
It's a city I would find on my own kind of deal with walking.
There's some lovely downtown neighbourhoods as well. The area around McGill is lovely. Westmount is the rich neighbourhood.
Restaurants galore. Restaurants everywhere. EVERYWHERE. Every kind of cuisine. Large Canadian cities - Toronto, Vancouver and Montreal - very multicultural. And Nancy some of these many restaurants are bring your own wine. Do you like that Nancy?

You can probably google that and actually get a website. Nancy with her own wine.
Most of my friends are still there so I'm not much help with hotels. I've stayed in Le Centre Sheraton years ago. Good central downtown location.
The Queen Elizabeth (you like Kelly?

) is an historic mainstay but I always feel that historic places are often small or out of date a bit to what people want in a hotel but I should be quiet b/c I haven't been in there for years.
I think it's a Fairmont now but don't quote me.
If you are okay with waiting I always use Priceline's Name Your Own Price (not the regular discount area - the one where you gamble to get low and don't know the hotel - just star level)
Is that the kind of blabbering you were looking for?