Did this ride last August with a friend. Parked at the Poughkeepsie train station. He took Metro North-need to get a bike pass online.
We stayed in Hudson, NY at a B&B. Lots of nice restaurants, nearby is
Olana which is the home of Frederic Church one of the premier Hudson River School painters (worth the side trip if you have time). Next day crossed to west side of the Hudson and connected 3 rail trails back to Poughkeepsie. Hurley Rail Trail, Walkhill Valley Rail Trail, Hudson Valley Rail Trail to Walkway over the Hudson.
Day 1-
Hudson RR Part 1
Day 2 -
Hudson RR Part 2 - A bike ride in Hudson, NY