Akshay: I buy one of their self-published novels here every time I come to Montreal
Matt: Picnic baskets filled with killer fried chicken and mason jars of craft cocktails, which they trust you to take over to the park across the street, enjoy, and return, blanket/plate/all. How Canadian!
Matt: Mile-Ex (pronounced "eeks") is the now-arriving Bushwick of Montreal, and this is its sprawling outdoor beer bar.
Matt: This is the best Lebanese (or Syrian) restaurant I've been to outside of Lebanon. Seriously. A bit fancy, but you can still get a walk-in.
Matt: You should grab a Bixie bike and cruise along the adorable Canal Lachine (with industrial ruins all along too) and then end up here for a local beer.
Matt: Best cappuccino in Montreal! Burly but kind Italian-French-Canadian baristas and a nice mini-terrasse outside. Great people watching. Where I start every day when visiting.
Matt: If you do one Museum, make it this one. Super progressive, focus on architecture and urbanism, in an amazing building slightly off the beaten path downtown.
Matt: It's a geodesic dome! Honestly, more a kid-oriented museum inside, but the Ile is beautiful and a good bike destination for a little exercise. Site of the World Expo '68
Matt: Massive outdoor greenmarket, lots of local produce. Too bad you'll be a tad early for blueberries!
Akshay: Almost forgot! You've got to get yourself some fresh Montreal-style bagels. Either here or at a Fairmount (locals have opinions about which they like better, but both are great!)
Matt: AK's note made me remember: This is the superior bagel place ;p Get some "all-dressed", Quebecois for "everything" but with the addition of caraway seeds (Honestly the two places are basically the same, but my friends have trained me to be a booster of this one)
Matt: Great pizza w/local ingredient focus, and they have a late-night takeout window on weekends