I've just spent another half an hour studying the trail maps. They don't get you in or out of the city, and they don't connect together in a continuous length by and large.
Not only that, the various trail maps I can find don't even correspond to each other! I have cycled down the Iron Horse Trail south to Cambridge and then down to the Grand River Trail to Brantford and Hamilton, but it was convoluted and a lot on roads I'd never repeat.
If you can link a map that "gets me out of town" for K/W, please do so. Even getting north to Elmira and on to the Kissing Bridge Trail has proven very difficult, last time I took a bus from the Conestoga Plaza....there's no way to cycle the main road north and have any nerves left.
It's truly unfortunate, as with the new LRT one would think there would be an effort to make K/W more enticing to distance cyclists, like Brantford, Hamilton, Petrborough and many other cities do.