Cinq à Sept

Happy hour is upon us! You can certainly enjoy drinks in that very specific time slot, but you're not limited to that! Deps and grocery stores sell alcohol until 11:00 PM, bars and restaurants can sell it until 3:00 AM. Now that you know the time, let's figure out the place.

Brasserie Harricana

Great food and excellent beers brewed right here in Montréal. Harricana takes great care in exploring beer styles and serving them at the right temperature. Not all beers should be served ice cold. This one's a bit further north than my other suggestions. Definitely make the trip if you're planning on visiting Little Italy.
📍95 Rue Jean-Talon O (Little Italy)

Pit Caribou

A lof of great micro-breweries in Québec can be found in Gaspésie. Pit Caribou is one of them. They opened a brew pub in the heart of Plateau Mont-Royal a few years back, to everyone's delight. From sours to IPAs, there isn't a style they don't do well. They also play around with spontaneous fermentation sometimes!
📍951 Rue Rachel E (Plateau Mont-Royal)

Brasserie Dieu du Ciel!

They recently renovated, double the size and added a large terrasse, yet it might prove difficult to score a couple of seats if you go during peak hours. They brew excellent and oftentimes unconventional beers, and they often have interesting guest taps. I haven't had the chance to try their new food offerings but heard great things.
📍21 Av. Laurier O (Mile-End)

Peluso

Ok so that one is neither a bar nor a pub, but a legendary beer store. They carry some 400+ local microbrews. If you love beer, this is a bit like paradise! If you go, make sure to grab something by Brasserie Dunham, they are one of my all time favorite breweries.
📍2500 Rue Rachel E (Plateau Mont-Royal)

Bar Henrietta

This is a cozy lounge with fantastic cocktails and small bites. The plates are perfect to share with friends, tapas-style. I love how they decorated the interior but I somehow always end up on the terrasse outside. Terasses are awesome.
📍115 Av. Laurier O (Mile-End)

A Place to Drink and Play Games?

You can do that pretty much anywhere if you have a Cubilete dice set, the game made famous at meetups by Chad. It's really fun, easy to learn and incredibly portable! Drinks and batteries sold separately. If you feel like adventuring a little though, here are the places to go!

Arcade MTL

All the fun of a classic arcade, except you don't have to put quarters in the machines, and there's video game theme cocktails and beers on the menu. The proprietor, Dominic Bourret (aka Papa Cassette), worked his butt off to get the city to reverse an old, outdated law that blocked barcades from being a thing. I'm glad he did! There's some great machines there, notably a Nintendo VS. System.
📍2031 Saint Denis St (Plateau Mont-Royal)

Ping Pong Club

I have a confession to make. I'm putting this bar in the games category but I've been there dozens of times and never played Ping Pong. I go there for the menu. They serve understated, elegant cocktails and tasty bites. I'm pretty sure you can still play Ping Pong there... I've seen the table! They had a Mississippi (Shuffleboard) table too, at some point. Might still be there?
📍5788 St Laurent Blvd (Mile-End)

Randolph Pub Ludique

Almost next door to Arcade MTL, Randolphe specializes in board games. They have an impressive selection of titles to choose from, and they serve both food and drinks!
📍2041 Saint Denis St (Plateau Mont-Royal)