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Tarrytown marina is right by the train station. Many of the eastern shore towns on the Hudson are convenient to their train stations from the river as the tracks often go right along the river.
In addition to October being the time of year they begin removing docks, it is also usually the time of year that the leaves start changing color. I would like to do a similar trip going only as far as Beacon; perhaps in mid-October or earlier.
Traveling up river with the tide is the way to go. You can be fighting a 2 knot current if you go against the tide.
Commercial traffic (tugs etc.) monitor vhf ch. 13 I believe.
"The Cruising Guide to the New England Coast" has a section devoted to the marinas on the Hudson.
Good luck, have fun and stay warm.
"The cure for anything is salt water~ sweat, tears, or the sea." ~Isak Denesen
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