I have to travel there for work in early Nov, and was thinking about possibly taking my board just to get a little early season riding in, especially since work is paying for my flight and hotel. I checked out the local places and honestly, they don't look like they're worth the trouble of hauling my shit up there.
I grew up in Manitoba. It's pretty much all flat prairie/lakes/tundra. Just by a quick google-maps it looks like your hills in Tennessee are better. If you want to jib some park then it might be ok. Within Winnipeg there isn't much, I know of one place called Spring Hill. Outside Winnipeg the better place is probably Assesippi (4hrs NW)
One thing I can't stress enough is to make sure you bring lots of warm clothing. Manitoba arguably is the coldest place in southern Canada so don't be surprised if it's extremely cold (I've seen temps in the -50s there) Have fun!
I live 15 mins outside the city. Spring hill usually opens around mid or early december so dont bring your board if you havent left yet. Plus its only fun here if you enjoy park or street, unless you play around in the sand/gravel pits like i do sometimes only steeps we have here.
Now continue on guys making fun of our flat geography...