Sir Winston Churchill - For those looking for the most famous watering hole in town, attracting all segments of society, Sir Winston’s, downstairs, or the smaller Winnie’s, upstairs, is where one goes. Sir Winston’s is the perfect bar to people-watch, both inside and out (from the terrace on either floor). Hollywood actors and professional athletes, when in MTL, always seem to navigate there for a drink, or ten. Keep in mind that it’s practically impossible to find a place to sit or stand, at times, but that’s beside the point. Getting into either club can be impossible at peak times, especially in the summer, so the cherished place of real estate one may actually find to sit or stand becomes valuable property. However, the idea is to actually get in, as it’s arguably the choice place in town to easily meet someone of the opposite sex. Although Montreal is mainly French-speaking, Sir Winston’s is located on Crescent Street, the English-speaking party downtown destination, with the club its centerpiece. The music mirrors what plays on the radio, mostly r&b, hip-hop, rock, and alternative, but the crowd and beverages are truly the only reason to be there. Hint: if there’s a line for Sir Winston’s, one can avoid waiting by first having a drink at Winnie’s!