Hudson is my beagle dog-in-law. He loves to go for walks in the Pawling (New York) Nature Preserve. He likes walking on the yellow blazed trail but he gets tired after a bunch of uphills. He likes the waterfall and the small bridge, then he likes to walk past the big rock overhang, then up and down some hills until he gets tired. He also likes to hide coffee cans with a camera in it. He suggests that you take a picture of yourself and leave it, when it is used up I will develop and post them.
Pawling has great little restaurant called McKinney and Doyle. 41 33' 42" N 73 36' 06" W. I recommend it for coffee or a meal.
These are nice walking trails, some ups and downs, not sidewalk easy, but not too hard either. Trails run near Appalachian Trail. Lots of nice walking in area. No public transit available.