I've travelled across most of this country, and have had some pleasant, as well as not so pleasant surprises.
From West to East:
Victoria - I was surprised that there was no beach within city limits.
Spokane Washington - the string of skywalks connecting buildings in the downtown core.
Medicine Hat - a veritable oasis in the heart of one of the driest parts of the southern Prairies. The river valley made for a scenic backdrop. I'm not sure I was expecting much of anything as we approached Medicine Hat - but I remember being pleasantly surprised.
Moose Jaw - at one time Moose Jaw was just as big as Regina or Saskatoon. I wasn't expecting to see larger historical buildings in the core of a town this size (i.e. especially compared to Grande Prairie)
Winnipeg - Incredibly Flat. In fact, Saskatchewan is almost mountainous compared to how flat I found it around Winnipeg. The only place I can compare this to is parts of the Netherlands. (p.s. Flat refers just to the geography, not the people!
Chicago - I had expected this to be somewhat of a gritty city, with a typical urban mix of 70's style Sears Tower (sorry Willis Tower) like highrises interspersed with parking lots and rundown smaller buildings. What I did NOT expect was the level of historical highrises, art deco detailing on buildings and walkability of the core. I could have easily spent a few more days in this city.
Hamilton - the number of historical buildings in Hamilton astounded me, especially since most Torontonians led me to believe it was an industrial armpit. Hess Village had a nice vibe with all the sidewalks pubs.
Guelph - I wasn't expecting so many older buildings in the core. Also, a lot of Ontario towns have redbrick, so Guelph's abundance of historical fieldstone buildings gave it a unique charm. The old fieldstone church overlooking the downtown not only provided great views, but also made a great photo opportunity in and of itself.
Niagara Falls - I wasn't expecting the level of kitsch, especially more pronounced on the Canadian side - but Clifton Hill was a riot, once we got ourselves in the right mood. I take visitors here all the time now.
Montreal - I had only ever seen pictures of downtown Montreal, so I thought their oldtown consisted of the older buildings on Ste. Catherines and Sherbrooke. Imagine our surprise on our second trip when we discovered the "real" old town
I've never been to Quebec City, as I'd tended to hear negative things about it... but based on some of the positive comments from certain posters - I'm thinking this city might become my next urban destination to explore in Canada.