Leto

Remember the time of year. Montreal is a great city to visit. French is not required, I've been there on a regular basis and have done just fine in English. Mind you, if you even give a half-hearted attempt to speak French, the locals will warm up to you, take pity and speak English.

But again, you will be there in the dead of winter. Montreal in winter is an experience. Make sure you are dressed for it. Tomorrow it will be minus 7 Celsius, and there is a lot of slushy snow on the ground, so you will need waterproof boots, a warm jacket and gloves.

Having said that, the city does have an extensive subterranean concourse (under ground city) similar to Toronto, that allows pedestrians to cover large areas without being exposed to the elements. It is also integrated with the subway system.

While you are there, and seemingly don't mind the winter weather, Quebec City is also close to NYC, and only a couple of hours (if that) from Montreal. This is a special city, worth the visit, and holds the Carnival:

From Wikipedia:

The Quebec Winter Carnival (or Carnaval de Québec), held yearly in Quebec City, Canada, is the biggest winter carnival in the world[1]. The festival typically starts on the last Friday of January or the first Friday of February and it continues for 17 days, usually with close to one million participants every year.

Quebec Winter Carnival - Wikipedia, the free encyclopedia

QC also provides cultural and architectural icons that are rarely seen in the 'New World'. The last time I was there, I saw the QE2 dock, and unleash a horde of tourists from NYC. Where ever you go in Quebec, if you do go, try the crepes. And Poutine. And the local cheese and beer.

As Highthief said, it's a no-brainer.

__________________
You said you didn't give a fuck about hockey
And I never saw someone say that before
You held my hand and we walked home the long way
You were loosening my grip on Bobby Orr

http://dune.wikia.com/wiki/Leto_Atreides_I