I'm hoping to take my father on his first-ever backpacking trip this month. He's only 62, but he's not in particularly good shape, so I'm looking for something rather trivial. Last year we dayhiked to the CT state highpoint together. With roughly 2000' of reasonably steep climbing, that turned out to be tougher than ideal, although he was able to make it. The idea for this trip is to enjoy being in the woods and spending the night out together. There's no particularly need to climb a peak or pound out serious miles, but clearly some nice scenery would be enjoyable. The general plan is to drive up from Long Island one day, spend the afternoon hiking, overnight in the woods, spend the next morning hiking some more, and returning that afternoon. We would consider a second night in the woods if necessary to complete an interesting loop. I'm not particularly worried about weather (short of snow), as I have plenty of warm gear to share and we are flexible with our dates in case of rain. The trip will probably include my girlfriend and my sister and we will be able to carry all of the camping gear, so my father can hike comfortably with perhaps only a bottle of water and a spare jacket on his back. Any recommendations would be appreciated, as I haven't been backpacking in the Catskills for over ten years.