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depends on many factors- strain selection, hours of direct light, latitude, sowing time, nutrients used, etc, etc. In general, auto's can be cut as early as late June/July...and regular, photoperiod strains, in Sept/October...
once bad weather hits, only certain, hardy strains with not mold up. first hard frost and it's game over for all pot plants. harvest windows vary greatly, esp outdoors. cut down when as rip as can be, without rotting...
i have some plants that grew from seed in my compost, without any help from me. they are right next to a shed under a tree. 5 frosts so far and 2 nights of snow have only ment more sugar and smell. i am cropping them on the weekend. mind you, under the conditions they are pretty protected, but, i have had to shake the snow off 2 days in a row
Have taken my harvest well past the first frost on a number of occasions. These were indica leaning, however they shook off the frost like it was nothing- 'cept it did bring out some lovely colours in the buds.
Far more of a concern- at least for me- is the chance of mould. Have been running till about the first week of Oct recently, as I had no experience with the strains I had been running, and did not want to risk the mould issue. As it was, I've found a few mouldy buds, but nothing serious. But where I will agree with Bigbag is that if you have a hardy strain, you can push well into October. It is those rainy days, with the lingering morning mist that encourages the mould in my experience. If the weather gods are cooperating, then I will push them as far as possible. But rarely have I run into Nov. Perhaps if you were on the shore of Lake Erie, as there is a gentler climate there- but not likely north of TO.
Keep in mind also- that a lot of the surrounding cover has lost much of it's canopy, and your plants begin to stick out like a sore thumb. You would have to be well concealed to run this risk.
It also depends on your AO and weather patterns etc. I've had plants survive a minor frost only to get gobsmacked a week later by what I thought was another minor hit... Wind + cold + frost has been a killer for me in the Interlake.
Pisses me off when we get a couple of minor hits, I chop...then we get 2 weeks of gorgeous weather.
I tented last year and it was too much a PITA for the few plants I bothered with.