I like a lot of the advice on this thread.
We went to Quebec City and then hit Montreal on the way back down in 2018.
I had been to Montreal several times while at SU but hadn't been back since I graduated in the early 90s.
As was noted by Eric and Ghost, Quebec City is just phenomenal and we definitely also thought it was Europe lite. Montreal is definitely fun though, and you'll have a great time.
Seeing the Rangers play at Montreal (and Toronto) is on my bucket list. Hope I can make that happen someday!
Our experience is always a little different because I have Celiac Disease and have to eat gluten free. That often means going outside of more popular areas.
Not sure what's going on with them in the winter, but the
Montreal Markets were awesome. Find some bakeries... we went to a gluten free one and it was one of the best we've ever been to after my diagnosis 15+ years ago.
Mondavie was our favorite restaurant. They had some live music that was great and the food was fantastic. We went to a couple steak houses, like
Vieux-Port , which were definitely good but we liked Mondavie better.
Order Poutine. Then try more Poutine. After that head out and find some Poutine.
Let us know how it goes!