In various conversations, it has been noted that an online bike trip planner that is similar to Winnipeg Transit's Navigo tool would be really helpful. (That is, in addition to an updated cycling map of Winnipeg!)
Vancouver recently launched a web-based route planner: http://www.cher.ubc.ca/News/MediaReleases/routeplanner_06-25-08.asp
Portland also has an online bike trip planner, which they describe as follows: "The byCycle bicycle trip planner is a free online tool to help both new and seasoned cyclists plan safe trips through the city. This private website was created by cycling enthusiasts volunteering their time, with support from Metro." http://tripplanner.bycycle.org/regions/portlandor
Something to think about for Winnipeg.