-- Last Updated: Mar-14-13 3:55 PM EST --
In whitewater I strongly tend to the cross-draw rather than the pry, primarily because that's the way I was taught.
In flatwater I use the pry in three circumstances often.
1. As a "bow jam" or "bow wedge" it is the quickest and most violent way to turn the canoe to the off-side. It is particularly useful to go around sharp curves in twisty streams. The wedge can be used used with either face of the paddle. To avoid being catapulted out of the canoe by the force of the prying wedge against the gunwale or hull, you can hold the paddle off the gunwale/hull with what Marc Ornstein calls a "Glarosian wedge", after Lou Glaros. The Glarosian wedge will give you stability support as the prying force of the bow jam/wedge kicks in.
2. As a necessary part of a prying sideslip. Sideslips one of my favorite moves, which I use to paddle among the overhanging branches along the shore of a lake or around the woody occlusions in a twisty stream.
3. During long days of straight ahead paddling I will sometimes use an off-the-gunwale stern pry as my correction of every forward stroke. Some will say this is an atrocity, but I like it for variety. Mason recommends it. I think some people call it the Northwoods stroke, but that may have other meanings too. Some dedicated users of this stroke wrap leather sheaths around their paddle shafts where the gunwale pries make their repeated impacts.
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