Would have been my sophomore year of college, when I drove up with a friend to Montreal for about three days. Went up with no real plan or anything booked, found and checked into a motel by the highway in Brossard (first time I ever booked a hotel myself), parked downtown and just wandered around.
At the time I had no idea that Montreal and Quebec were actually French-speaking. I thought it would be like New Orleans, with a historic French link that has nothing at all to do with everyday life. When we crossed the border, English disappeared from the signs, and the radio turned entirely to French, I was pretty damn surprised.
I wish I could say I got into mischief, but we didn't even go to a bar, as far as I can recall. I think we just wandered around downtown and Old Montreal; not even sure we took the Metro or went to the Plateau (which is my home away from home there now.) The things 19-year-old me should have done...