Montreal's winters can be utter misery, ending with what Lenny Cohen called the April autopsy, when all the ugly mushy stuff below the snow finally becomes visible and glory begins to thaw. But that said, there's plenty of glory below the frozen tundra. Like, a lot.
Grand Prix Weekend: F1 Weekend transforms the island city into a magnet for racing fans, Eurotrash, and hookers (yes, even more than normal!). It's such a cash cow that a succession of mayors have had to kiss Bernie Eccleston's backside for a mere guarantee to keep it going. Check out racing car street fairs on Crescent. And in other parts of the city, hotel prices will skyrocket.
Jazz Festival: A sea of see-and-be-seen events jam the summer calendar, none better than the jazz festival, which takes over the streets for two weeks at the end of June and always comes with great and not-so-great musical freebies. Even if jazz isn't your genre of choice, the festival attracts massive crowds and artists like B.B. King, Aretha Franklin, and Ray Charles (obviously before he died).
Carifiesta: Though it lasts just two hours on a Saturday in July, this parade celebrates all things Caribbean; basically, it's a Canadian version of Carnival. Drum beats and dancing, semi-clad Caribbean babes take over downtown Montreal just for your watching pleasure. What's not to love?
Hockey season: Foot-bladed men crash into one another (on purpose!), while trying to slap a rubber disc into a net. Sure, Americans might not fully understand why Canadians are crazy about hockey. But pop in for a Canadiens (call them the Habs) game against Boston, and you'll quickly understand the depths of passion this city feels for its sport. Mullets not required.
Winter: Yes, babes really do stand outside of clubs on freezing nights, bare-legged in cocktail dresses. They're Canadian, so they're accustomed to the cold. They grow 'em hearty up here. Hotel bargains can be had on off-season visits, so you'll have more dollars for the ballet, and first-class skiing is just a couple of hours drive. Don't sleep on the cold months.