Well, if you haven’t hooked up with any of the following hacker/creator communities yet, you should definitely do so. Lots of interesting groups have been coming out of Winnipeg for the past few years.

SkullSpace (WIP hackerspace): http://www.skullspace.ca/

Secret Handshake (monthly meetup for freelancers): http://www.meetup.com/secrethandshake/

Winnipeg.rb (Ruby group with a monthly meetup): http://winnipegrb.org/

Winnipeg WordPress Meetup (organized by a local Automattic employee): http://winnipegwpmeetup.wordpress.com/