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My brother recently told me a story that when he was 18 he and a few friends popped a tent on the island while drinking and popping acid. They set up in the wooded area on Ward's Island near the Eastern Gap and were chased by an Island resident who was awoken by the noise. Eventually they woke up five hours later sans tent in and around Hanlan's Point.
 
You can only paddle the Don during the annual "Paddle the Don Festival" (which I've wanted to go to for sooo long - apparently spots fill up super-fast). Normally, the river is too shallow in parts and you would need to portage/drag through. But for the festival, they release a gate of water onto the river in the morning so paddlers can enjoy deeper water for basically their trip down and their trip down only.

Likely some parts are deep enough any time of year, but you wouldn't get much of a day's paddle out of it.

Sort of irrelevant but I paddled the Grand a while back from Cambridge to Paris and it was really pleasant. If you're just looking for a close-ish river to paddle.

And a friend of mine worked at an Outdoor Ed centre owned by the Toronto District School Board on one of the islands a while back. Maybe that's where the Scouts camp? If you look at islands other than Centre Island, you may have more luck with camping.
 

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