If you are unfamiliar with an area, your best bet is to check paddling guides like those from the Appalachian Mountain Club, ADK and similar publications for other regions. Things are moving here - a section of a long-used canoe passage was blocked for quite a while by new owners of adjacent properties and the court just upheld paddler's rights there within the last year. Newer property owners are being a problem in many areas where no one ever thought about it before.
Also, do NOT assume that you are good up to the high water mark everywhere. There are a number of states that use a lower point, for example in Maine it is mean low tide. That means officially you can't pull out on some inviting but private island except for maybe an hour during daylight, on a very low tide day. Curiously, if you are doing it to check out your navigation and plot a course, or fish, you can go a bit higher. It is good to always carry paper charts in Maine even if you don't know how to use them, because they are more compact than a fishing pole.
Recreational Kayak Paddle
Heel and Pegpads™
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