McGill educated Yank here. Born in Kennebunkport Maine, a lovely town about 7 1/2 hours from Montréal - my favourite way to do it? via Dixville Notch NH. An overnight at the beautiful Balsams resort there is glorious; of course there are great places in the Eastern Townships too (my fav' on Lac Megantic), but we're talking New England here.
Portland is actually a really hip town these days with several art schools in the area, and lots of craftspeople all around. Restaurants like Café Uffa, Fore Street Grill and Walters serve excellent food a very nice atmosphere and won't break the bank.
As for my hometown, Kennebunkport, despite the unfortunate summer retreat of some of our least talented US presidents there, nice places to stay and eat there too, and some lovely beaches if that's what you like. My lodging recommendation would be the Maine Stay right in town; they have a website, but not sure the URL. For dining, there is the internationally acclaimed White Barn Inn, a bit rich and heavy for my tastes, but most ppl who go there rave about it. We also like Windows on the Water for fancy, and for casual there is Mabel's Loster Claw (for lobster of course) and also Federal Jack's (a brewpub and home of the various Shipyard beers, decent food too) and the ever popular Alisson's right downtown (just near everything).
As for outlet shopping, we generally go to Kittery ME for variety and good prices, and have generally found North Conway too crowded most times (only one road snaking thru, and not very good restaurants for the most part). Freeport is nice with the LL Bean outlet and the main store as well (also pretty miserable dining options there, but at least you're near Portland). We don't know Stowe well, but understand it is lovely; we also like the tour at Ben & Jerry's Ice Cream down the road from there in Waterbury (Yum! and really fun).
Alas I cannot live in my home State of Maine, nor my favourite city, Montréal, so we're sticking with our third choice, Boston (at least we have decent baseball here). Enjoy!