What a challenge that would be... I bet some crazy local cachers will take you up on the challenge.
Looking at TravelingGeeks Bookmarked list, it looks like Prince Edward Island would be one of the next destinations for the power-trail hungry crowd! There are 962 caches on the C.T. (Confederation Trail) series, plus another 85 caches on a "spur" off of it. http://coord.info/ma...-62.853732&z=10
The bad new is....it's a hiking/biking trail only. Doubtful you could get 1000 caches in a day, sans automobile!
Well yes if you are into that sort of thing. However I am!