Where to party in Montreal? Here are some travel tips by a local:
Please do not go to the typical tourist traps that websites tell you to. The only people you will meet are other tourists and underage teens who leave at 1am. Montreal is known for our beautiful women and well-groomed men - here is where to find them, depending on your style!
Crescent Street: Not the GREATEST area anymore, as it sees mostly the older set and can be expensive...it is kindof known as the street that used to be cool. However, Brutopia has a nice selection of beer and good live bands, and Sir Winston Churchill pub can be decent depending on the night. If you are a young guy looking to pick up a "cougar" or 2, check out Thursday's - trust me. McKibbin's Irish Pub and Irish Embassy (on Bishop, a street over) are quite good. After a late night on Crescent, everyone flocks to "Boustan", a lebanese fast food place that is truly the gem of this street - worth stopping by (order the shish taok). Stay far away from the clubs here unless you actually are underage. "Light", "Seven" etc are overpriced, gross and full of jailbait.
St. Laurent Street (aka, to some people, The Main): This is my go-to area on any night really. Check out the bar Biftek (above Prince Arthur) for cheap drinks and a hipster university crowd, as well as Jupiter and Blue Dog for more of the same. A great starting point. Check out B-Side (but ONLY on thursdays, they'll keep guys waiting outside on weekends and tell them its "full") for old school jams. Have a "moonshine". Tokyo is worth it on Sundays or Thursdays as well, if you like dancing and a more clubby atmosphere that is not pretentious, just fun. They have an awesome terrace in the summer. If you like high end supper-clubs that are expensive with no-so-great food (but the people are beautiful) Globe and Buona Notte (above Sherbrooke) are popular with visiting celebrities, hockey players and wealthy businessmen. Way up St. Laurent is Chez Serge, where you can ride a mechanical bull and drink from a bucket - need I say more? The Sparrow is also popular with the hipster crowd, and right across the street. The hands-down best late night eats is the 2$ peanut-butter noodles (close to Biftek). No night is complete without them! The place is small and hole-in-the-wall but everyone loves it. Ask any local and they will tell you where to find it. La Belle Province is also a good choice for our classic poutine.
The Plateau/Rue. St. Denis: St. Denis Street is known as the "french" St. Laurent. There are lots of nice bars...Distillerie is a great little place but you must get there early as it gets packed with young and hip Montrealers any night of the week and it is quite small. bar St. Sulpice has the BEST and biggest terrace in the city and can always be counted on for a good time - the place is really big and they serve good food late. Bar St. Elizabeth is also worth checking out, especially in the summer. The Plateau is without a doubt one of the most stylish and worthwhile areas to experience nightlife. Billy Kun is always good for a quality night, as well as Blizzarts for its theme nights. Baldwin Barmacie is also a classic any night of the week: strong drinks, a cool crowd and the best mac&cheese ever. La Banquise is the holy grail of poutine restos and is open 24h - go there without fail.
Old Port/Vieux Montreal: this place has some really cool clubs and bars, on the more expensive side compared to St. Laurent, but much better quality and a less touristy vibe. My favourite restaurant that turns into a bar/club later on is Garde Manger. The food is phenomenal (the chef is Chuck from Food Network), but yes, a bit pricey. It is hard to get reservations last minute so call ahead but trust me...totally worth it. Also a location to see and be seen. Santos is a supperclub that has good tapas and a pretty crowd. Le Confessional is a dimly lit, hip bar with dancing and reliable for a fun night with a group. Pretty much any bar you go to here is bound to be good, but make sure: no sporting running shoes and baseball caps! It's a classier area than Crescent & St. Laurent.
Other: If you are looking for a super cheap, dirty night and are of university age go to Reggie's. It's Concordia University's student bar and thursdays are their Dollar Beer nights. Make sure to go early and bring ID, but it's always fun and always messy (in the best way possible). Please do not try to go there if you are over 24-25... you either won't get in, or people will stare and think you are a creep (male or female!)
Other than that, eat smoked meat at Reuben's or Schwartz's (the classic), have poutine at La Belle Province, a chocolate sundae at Juliette et Chocolat and just enjoy yourself.
Montreal is at its best in the summer, but a bit of snow doesn't stop us locals from having fun. Don't forget to tip, be friendly, and you are guaranteed an amazing time.
Here is another travel tip I wrote about: What to see & to do in Montreal