I currently live in Montreal so if you have any questions regarding the city, let me know.
A few notes about Montreal:
The party scene here is anything you want it to be. I personally would recommend staying away from the Crescent Street area because it is more expensive and is the ‘touristy’ area. I would recommend checking out the following streets. (they are all connected, so you can walk up st-denis, then east on mont-royal, then south on st-laurent till you hit prince-arthur…)
St-Laurent (north/south): This street has a surplus of bars, clubs, nightlife. You will probably spend a night or two bar hopping here.
Mont-Royal (east/west): This street has a lot of great bars that are a little more relaxed then the trendy hype you find on St-Laurent. We regular this area…
St-Denis (north/south): This street has lots of shopping, restaurants and some nightlife.
Prince-Arthur (coble stones): The intersection of St-Laurent and Prince-Arthur is a very happening place. Lots of tourists because of the patio restaurants on the coble stone street that is closed off to cars, but this area is also one of the central hubs for nightlife in Montreal.

The next important question is “when are you coming?”. Jazzfest is one of the best times to be in the city. There are hundreds of free shows throughout the downtown area and the city is electric. Since that starts tonight, I doubt you will make it for that, but there are usually festivals or free stuff happening all summer here. When you get to the city, check out the “Hour” (and their website) newspaper. It is a free english paper that is packed with upcoming events and festivals etc…

In terms of transit to get to Montreal, its not going to be much fun. The bus ride from Boston to Montreal is about 8 or 9 hours and can get pretty boring. It is however a very cheap option, so I have done it 4 or 5 times. I usually do it overnight and try to get some sleep (good luck). Last I checked there are no trains from Boston to Montreal. I think there is one train that goes from NYC to Montreal, but I was getting conflicting information from the companies last time I tried to research it.

Ask away if you have more questions…

Thanks Will!

Heading up there next weekend from NYC. Looked into both rental car and train (for 4 of us). Rail is like $60 each way, not too bad but going by car will be a little cheaper and much quicker.