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October weather is sometimes dicey... the monday of that week is our Thanksgiving (I believe it is usually the 2nd Monday in oct) but in the last few years it's been spectacular for weather for walking around.
Charl will prob take you around MuchMusic, Queen street, Spadina with Chinatown. And maybe the Eaton Centre for some crass commercialism and major people watching. The big radio stations are all along the strip there too (CFNY - the Edge, Q107 Classic Rock ) as well as the Hard Rock Cafe...
You should go for a walking tour of the University of Toronto campus as well. In the fall, it is gorgeous.
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