Debates about the relative merits of Toronto versus Montreal are rarely level headed. Each city has its champions and its detractors and, unfortunately, the loudest are often the least objective, having only ever lived in one city or the other, but not both.
I've lived in both, for extended periods of time, so I feel I'm in a better position than many to dispense some useful observations on Canada's two largest cities.
Observation #1: Toronto is much bigger than Montreal, and feels like it, too
On a warm day, you can walk lengthwise from one end of downtown Montreal to the other without really breaking much of a sweat. You'd be hard-pressed to do this in Toronto. The situation is made more extreme by the fact that a large chunk of the island of Montreal is taken up by an airport. So the amount of usable space in Montreal is even less than the size of the island might suggest.
Observation #2: Montreal feels smaller than it actually is
Montreal actually has a pretty hefty population - it is Canada's second largest city after all - but it doesn't feel like a large city in the sense of, let's say, New York or Toronto. It's difficult to pin down why this is, though that won't stop me from trying.
First, for whatever reason, Montreal has less of a corporate "chain" culture than a place like Toronto. Yes, it's got Starbuck's and Domino's but...less of them, supplemented with a prominent splash of local brands and one-off Mom and Pop shops.
Second: there's the language thing. Most people in Montreal, I suspect, identify themselves as Anglophones or Francophones, but not so often as bilingual. This has an effect on how big the city feels. Take a store like Chapters. Chapters sells primarily English books. Other stores in Montreal, such as Archambault, sell primarily French books. People tend to frequent one or the other, so while there might be four major bookstores in the downtown core, it feels like there are only two.
And it's not just stores. Neighbourhoods in Montreal are often unofficially classified along language lines. The West Island is usually seen as "English". Hochelaga is often labelled as "French". It's not unusual for someone to avoid frequenting a neighborhood because of the language - often unconsciously. This makes Montreal seem smaller than it really is.
I'm not sure if this is a "win" or not. Montreal is a large city that feels like a small town, which can be charming, but at the same time it feels like certain parts of the city are "locked off".
Observation #3: Montreal feels a lot bigger than it is
This is at odds with observation #2, so I should probably explain. Certain areas of Montreal have an extremely high population density; if I had to guess, for example, I'd say that the Plateau is one of the most densely populated areas in North America. Compared to other neighborhoods in Toronto, the Plateau is always bustling. Urban sprawl is something you tend to see less of on the island of Montreal.
The high density and extreme hustle and bustle of certain neighbourhoods contributes to the sense that there is just a lot more going on in Montreal as compared to Toronto.
Observation #4: There are a lot more jobs in Toronto than Montreal
This isn't surprising; the language laws in Quebec are a turn off for many large companies. Sure, you might open a branch of something in Montreal, but a head office? Not as likely. If you're going to set up a Canadian office for some large corporation, and you have to choose a city, you're probably going to pick Toronto over Montreal.
Consequently, people tend to be more career oriented in Toronto than in Montreal. Again this isn't surprising, since there are more jobs to be had there, but it does lead to...
Observation #5: Montreal is more fun than Toronto
Obviously "fun" is subjective, but this flows from the "Torontonians are more career oriented than Montrealers" statement, which is fairly uncontroversial. There is more of a "work to live" attitude in Montreal. And bars are open until 2am, the latest in the country.
Observation #6: Toronto is more cosmopolitan than Montreal
This one's a biggie. As cities go, people often classify Montreal as more "European" and Toronto as more "American". That can mean lots of things, from Montreal having nicer churches to Toronto having more chain stores, but one big way that this classification rears its head is in each city's demographics.
Montreal consists of about 26% visible minorities. Toronto consists of about 43% visible minorities. The difference is even more striking when you look at the Greater Toronto Area versus the Greater Montreal Area. People project that, within a decade, the term "visible minority" will be a misnomer when applied to Toronto. As Bowser and Blue wrote: "What's Toronto got that Montreal has not? A Chinatown you don't miss if you blink".
Toronto is one of the most multicultural cities in the world. Much like New York City, you can find pretty much anything you want there, no matter where it's from. This isn't the case in Montreal. Staples of Torontonian life, like dim sum and roti and Caribana, are just much less common in Montreal.
Compared to Torontonians, Montrealers tend to be more...how shall I put this...race-aware? It's not racism, exactly. It's more that one's race in Montreal forms a bigger part of one's identity than it would in Toronto.
Here's an example: when I moved back to Montreal, the company I worked for hired an organization called "Destination Montreal" to help me find a place to live. When I mentioned that NDG was a possibility, my guide said "Okay, but you do realize that a lot of black people live there, right?". There was no particular rancor in his voice; he was just a stating a fact.
Another example: Evelyn and I were having dinner with a friend of hers, a former Montrealer visiting from Vancouver. As she started to describe what Vancouver was like, did she focus on the mountains, or the ocean or the buildings or the general vibe of the place? No, the very first thing she said was "Asians. Lots of Asians". Again, there was no rancor there, just an observation. But it was the first one she had.
I attribute it to what I call the "city pigeon" syndrome. You know how city pigeons are kind of oblivious to people because they've gotten so used to them? It's like that. When almost half your city consists of non-Caucasians, you tend not to notice anymore.
Observation #7: your mileage may vary with all these observations
These were, more or less, my experiences. If you've had different ones, you should, of course, let me know! I'd be very interested in hearing them.