Try Montreal. It has a strong focus on both French and English, so it has that kind of European feel. The people are very socialist and liberal, and there is a big artist and gaming scene there. Yearly, there are multiple festivals including the International Jazz Festival, the Formula 1, Igloofest, Les Fêtes Gourmandes, Le Festival de la Bière, and much much more.
It is a very happening city, with alot of very beautiful girls from all over the world. Ubisoft has one of its main offices there (The makers of Prince of Persia, Splinter Cell and Assassin's Creed).
In the summer is when the city comes alive, it can get dull during wintertime. During summer, every sunday, there is an event on the central mountain (le mont-royal) where people bring tam-tams and play to the beat all together (in the 50s of people). You have people who play haki, soccer, juggling, just people relaxing.
Summertime is really happening in Montreal.
Other than that, I know that Toronto is a hub for some of the most important activities in canada, like TV show shooting, TV News offices, but from what I saw Toronto is a very busy city. However, it has lots of Galas that are more up-scale than Montreal's, like Movie Galas and such.
Vancouver has it all: mountains, water, city life. It would be my next suggestion after Montreal. In the end, it all depends on what you're looking for.
New England is a beautiful area, I personally live in Fredericton (just north of Maine), and though it can get quiet here, it is also peaceful at the same time. I'm not so familiar with the states of New England, but I think there's a similar vibe down there where everything is just going okay and the weather is not too bad.