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Whenever JOOF comes to town he usually starts off his sets quite proggish. He's actually doing an extended 8 hour set or something at Toika this August (http://www.tranceaddict.com/forums/...s=#.U97lFvldUnU). Given that this event is just JOOF playing the entire night, I guarantee you he'll be playing more prog earlier on, as he's essentially the opener, peak-timer, and closer.
Other than that, the late 90's early 00's house sound, specifically prog, is a rarity in almost every country nowadays. I honestly don't think you'll be able to find a regular night like that at a venue in Toronto anymore, unless a special event is thrown (I think Houseaddict (?) used to have a monthly event of old prog like this but I don't believe it's happening anymore). Most DJs in Toronto have been around, especially the veterans, and they have extensive collections from that era and have played that stuff in the PAST, but not in the present.
You might be able to hear that sound at an off-chance at Cherry Beach on Sundays, but you'll have to do some investigating.
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